Chelsea holiday lettings

We found 2,917 holiday rentals — enter your dates for availability

Discover a selection of 16 apartments and other holiday rentals in Chelsea that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, which might include a pool and a washer and dryer. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chelsea

Showing deals for:22 May - 29 May

Image gallery for Ultra-Rare 12BR Compound • Sleeps 40 • Events

Outdoor dining
9.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)

Ultra-Rare 12BR Compound • Sleeps 40 • Events

Boston

8% off
Price is £27,241
for 7 nights, 1 home
£3,892 per night
includes taxes & fees
Ultra-Rare 12BR Compound • Sleeps 40 • Events

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Why visit Chelsea

  • Cultural attractions: Discover historic sites like the Chelsea Theatre and the magnificent Chelsea townhouse, showcasing the city's rich heritage.
  • Urban parks: Enjoy the green spaces and parks that offer a refreshing escape within the bustling city environment.
  • Family-friendly activities: Engage in various activities suitable for all ages, ensuring a delightful experience for families.
  • Diverse accommodation: Choose from a range of stylish apartments and modern condos, perfect for any type of getaway.
  • Welcoming atmosphere: Experience the friendly locals and vibrant charm that make Chelsea a unique and inviting destination.

Popular types of accommodation in Chelsea

Discover the charm of Chelsea with our selection of holiday rentals, including houses, stylish apartments, and modern condos. Whether you're seeking a family getaway or a romantic escape, Chelsea offers a variety of accommodation options to suit your needs. With our transparent booking process, you can find the perfect place to stay while enjoying the vibrant culture of London. Explore the best Chelsea holiday rentals today!

  • Houses: The top choice for visitors to Chelsea, these spacious homes offer a comfortable and private retreat for families or groups.
  • Apartments: A popular selection for those seeking convenience, apartments provide a homely atmosphere right in the heart of Chelsea.
  • Condos: These modern accommodations are ideal for travellers looking for a blend of luxury and practicality during their stay.
  • Cottages: For a quaint and charming experience, cottages are a delightful option for a peaceful getaway.
  • House Boats: Unique and picturesque, house boats offer a distinctive stay on the water, perfect for an adventurous experience.**

Top attractions near Chelsea

Chelsea, Massachusetts, is an excellent destination for those seeking city, business, and cultural experiences. Visitors can explore urban parks, historic colleges, and event venues that cater to families and culture enthusiasts alike. Notable attractions include the magnificent Chelsea townhouse and the Chelsea Theatre. This vibrant city promises a delightful blend of history and modernity, ensuring a memorable visit.

  • TD Garden: A premier event and conference venue located 1.2km from Chelsea, TD Garden is the heartbeat of Boston's sports and entertainment scene, offering a vibrant atmosphere for thrilling concerts and games.
  • Boston Common: Situated 1.9km away, Boston Common is a sprawling urban park perfect for families, featuring lush green spaces, walking paths, and playgrounds, ideal for outdoor activities amidst the city's hustle.
  • Copley Square: Just 2.5km from Chelsea, Copley Square is a modern hub of city life, surrounded by stunning architecture and bustling shops, providing a lively atmosphere for both locals and tourists alike.

Things to do recommended for couples

For a romantic getaway in Chelsea, explore the vibrant House of Blues Boston for a memorable concert, enjoy adventure at the Courageous Sailing Center, or immerse yourselves in culture at the Jose Mateo Ballet Theatre. Each offers a unique experience just a short distance away.

Things to do recommended for families

Families can explore the exciting LEGOLAND® Discovery Center, just 1.2km away, or enjoy the sports atmosphere at Agganis Arena, 3.1km distant. For a touch of wonder, visit the Charles Hayden Planetarium, located 1.9km from Chelsea, offering engaging entertainment for all ages.

Things to do recommended for groups

Groups visiting Chelsea can enjoy the vibrant atmosphere at Faneuil Hall Marketplace, just 1.2km away, indulge in cultural performances at the Wilbur Theatre, 1.9km away, and savour local produce at the Boston Public Market, also 1.2km away, offering a delightful taste of the region.

What do I need to keep in mind when booking a vacation in 'Chelsea

If you’re travelling with a group, family, or pets, or if you’re seeking extended stays, it’s essential to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chelsea with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chelsea with young kids: Traveling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as seek out age-appropriate facilities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Chelsea: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chelsea: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right destination. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Chelsea

Discover the vibrant charm of Chelsea, Massachusetts, where city living meets rich culture. Enjoy family-friendly activities and friendly locals as you explore the urban atmosphere. Venture into nearby neighbourhoods for historical sights and delightful holiday lettings. Whether you're seeking a business retreat or a leisurely getaway, Chelsea offers upmarket experiences and a welcoming vibe perfect for your next adventure.

  • Boston: Boston is a vibrant metropolis located a mere 1.9km from Chelsea. Renowned for its rich history and cultural diversity, this city offers an array of activities suitable for families and culture enthusiasts alike. Visitors can explore prestigious educational institutions, attend exhilarating music concerts, and indulge in shopping at various mall centres. Notable landmarks include historic sports stadiums and conference venues, making it an ideal destination for those keen on experiencing the city's dynamic urban lifestyle.
  • Downtown Boston: Just 1.9km away from Chelsea, Downtown Boston is a bustling neighbourhood that perfectly encapsulates the city's charm. It is a hub for culture, family activities, and urban exploration, drawing visitors for its vibrant shopping centres and educational opportunities. Attractions such as stadiums and historic sports venues enhance the area's appeal, offering a unique blend of history and modernity. This lively neighbourhood promises an enriching travel experience, immersing you in the heart of Boston's cultural scene.
  • Cambridge: Located 2.5km from Chelsea, Cambridge is a city steeped in academic excellence and cultural richness. Home to prestigious universities, it attracts visitors seeking educational and family-friendly experiences. The city boasts a variety of shopping centres and vibrant activities, perfect for those looking to explore. With highlights such as historic college campuses and stadiums, Cambridge offers a delightful mix of historical significance and contemporary charm, making it an essential stop on your Boston itinerary.

Best time to go to Chelsea

If you're planning a trip to Chelsea, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnySlightly LowSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyAverageSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageSlightly High
September65.7°F (18.7°C)Light RainMostly SunnySlightly HighAverage
October55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
November44.4°F (6.9°C)Light RainMostly SunnySlightly LowAverage
December36.3°F (2.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can achieve considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up from where you last stopped, or review and arrange your travel itineraries. Any properties you’ve previously saved or booked can now be easily accessed under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The natural setting of Chelsea is ready to explore

Learn about the unique charm of Chelsea with a stay in a holiday home rental. Well known for its restaurants, shopping and bars, this welcoming city won't disappoint. Fenway Park and Encore Boston Harbor are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Chelsea

Do you want to find attractions to see in the city? Venture out of your holiday home and check out everything that makes Chelsea a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (1.9 mi / 3 km)
  • New England Aquarium (2.4 mi / 3.9 km)
  • LEGO® Discovery Center Boston (2.4 mi / 3.9 km)
  • Harpoon Brewery (3.1 mi / 5 km)
  • Boston Marathon Finish Line (3.7 mi / 6 km)
  • The Fens (4.9 mi / 7.9 km)

Exploring the natural features in Chelsea

Whether you're an active traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Chelsea. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (3.1 mi / 4.9 km)
  • Copley Square (3.6 mi / 5.9 km)
  • Boston Harbor (2.2 mi / 3.5 km)
  • Revere Beach (2.3 mi / 3.8 km)
  • Rose Fitzgerald Kennedy Greenway (2.4 mi / 3.9 km)
  • Charles River Esplanade (3.1 mi / 5 km)

Transport options to and around Chelsea

The nearest airport is in Logan International Airport (BOS), located 2 mi (3.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 2.1 mi (3.4 km) away.

If you'd prefer to travel by train, the main station serving the city is Chelsea Station.

Frequently asked questions

What is the best area to stay in Chelsea when booking a holiday rental?
When considering where to stay in Chelsea, Massachusetts, a great option is the Chelsea waterfront area. This location offers a charming blend of urban convenience and scenic views along the Mystic River. Visitors can enjoy leisurely walks or bike rides along the waterfront, making it an appealing spot for those who appreciate outdoor activities.

Another vibrant neighbourhood to consider is Chelsea Square, which boasts a variety of local shops, cafes, and restaurants. This area provides a genuine taste of local culture, superb for holidaymakers looking to immerse themselves in the community. Not far from Chelsea Square, you can also find the Chelsea Market Basket, a popular grocery store that offers a wide selection of fresh produce and local goods.

In terms of attractions, the nearby Bellingham-Cary House, a historical site, gives visitors insight into the area's rich history, while the Chelsea Greenway offers lovely green spaces ideal for relaxation. The waterfront area features a limited but varied selection of holiday rentals, ranging from modern apartments to charming homes, suiting different tastes and budgets.
How much does it cost to rent a holiday home in Chelsea?
Prices for holiday rentals in Chelsea vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chelsea to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chelsea holiday house rentals?
You can find great discounts on house rentals in Chelsea on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chelsea?
For renting a beach house in Chelsea, Massachusetts, the best options can be found along the nearby coastline of Revere Beach and Winthrop. Revere Beach, known for its long sandy stretch, offers various holiday rentals with amenities tailored for beachgoers. Many properties here come equipped with outdoor spaces like balconies or patios, providing superb spots to enjoy the sea breeze and views. Several beach houses also feature modern kitchens, allowing for easy meal preparation after a day spent enjoying the sun and surf.

Moving towards Winthrop, the area presents charming waterfront properties that often include easy access to the beach, private decks, and family-friendly amenities. This neighbourhood is known for its quaint, small-town atmosphere, and many rentals are within walking distance to local eateries and shops, enhancing convenience for visitors. Additionally, Winthrop's proximity to the Boston Harbour offers opportunities for scenic walks along the waterfront and access to ferry services to downtown Boston, making it an attractive option for those looking to combine beach relaxation with city exploration.
What is the most popular type of holiday rental accomodation in Chelsea?
In Chelsea, apartments are the most popular type of holiday rental, with around 27 available throughout the city. These apartments are typically situated in lively neighbourhoods, offering easy access to local amenities and attractions. Most feature modern conveniences such as fully equipped kitchens, comfortable living areas, and often laundry facilities, making them suitable for both short and extended stays.

Additionally, there are approximately 12 condos available, which tend to provide similar amenities and are often located in well-maintained complexes, sometimes with communal facilities like pools or fitness centres. For those seeking more space, there are several holiday houses that cater to families or larger groups, usually offering multiple bedrooms, private gardens, and outdoor seating areas for relaxation.
Are there any family house rentals in Chelsea?
In Chelsea, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhood is conveniently located near Boston, allowing easy access to attractions such as the Boston Children's Museum and the New England Aquarium, both of which are ideal for family outings.

Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play. Additionally, visitors can expect amenities like Wi-Fi and laundry facilities, ensuring a comfortable stay.

As families explore the area, they'll find parks and playgrounds nearby, great for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Chelsea?
In Chelsea, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This vibrant city, located just across the river from Boston, provides a unique blend of urban living and access to nearby recreational activities. Many properties come with amenities such as private pools, hot tubs, outdoor seating areas, and fully equipped kitchens, making them ideal for relaxation and entertaining.

While enjoying your stay, you can explore the local dining scene and cultural attractions in Chelsea, as well as take advantage of the proximity to Boston's many offerings, including parks and waterfront activities.
Can I find long-stay holiday rentals in Chelsea?
A long-stay holiday rental in Chelsea is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chelsea?
In Chelsea, visitors can find several pet-friendly house rentals that cater to a variety of needs. The area offers convenient access to Boston, making it an ideal base for exploring the city while enjoying the comforts of home. Many of the holiday rentals in Chelsea come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, superb for both relaxation and entertaining.

Nearby, the Chelsea Greenway provides a lovely setting for walks with pets, featuring paths and green spaces that make it easy to enjoy the outdoors. Additionally, the area is close to the waterfront, where you can take leisurely strolls along the Chelsea Creek, offering a scenic backdrop for pet owners.
Are there any remote work holiday rentals in Chelsea?
In Chelsea, Massachusetts, there are numerous remote work-friendly holiday rentals available, with about 39 options to choose from. Many of these properties cater specifically to those needing a conducive work environment, featuring amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and printing facilities. This makes it easy for travellers to balance work and leisure during their stay.

The neighbourhood is conveniently located near Boston, offering quick access to a vibrant urban setting filled with cultural attractions, restaurants, and parks. While enjoying their stay, guests can explore nearby points of interest, including the Chelsea Market, which is superb for sampling local cuisine. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chelsea holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chelsea with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chelsea?
In Chelsea, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals comfortably. Many properties come with a coffee and tea maker, which is superb for those who enjoy a morning brew. Additionally, blenders are often provided for making smoothies or other beverages. Outdoor spaces such as decks or patios are common, offering a pleasant area to relax and unwind. Importantly, many rentals in Chelsea are pet-friendly, making them suitable for travellers who wish to bring their furry companions along.
When is the best time to visit Chelsea for a holiday rental?
The best time to visit Chelsea, Massachusetts, for a holiday rental is during the peak season from May to July. This vibrant period attracts visitors keen to explore the city's rich history, diverse culture, and proximity to Boston. July, in particular, stands out as the most popular month, offering warm temperatures averaging around 24 to 30 degrees Celsius, superb for outdoor activities and sightseeing.

During the summer months, you can enjoy Chelsea's waterfront parks, local markets, and various festivals, all of which contribute to an energetic atmosphere. The city is abuzz with tourists, creating an exciting environment for those seeking socializings and community events.

If you're looking for a more budget-conscious option, consider visiting in November. While the weather is cooler, with temperatures ranging from 0 to 10 degrees Celsius, this month provides a unique opportunity to experience Chelsea without the crowds. You can enjoy quieter walks along the waterfront and explore the local dining scene at a more leisurely pace.

Ultimately, the best time to visit Chelsea hinges on your preferences—whether you desire the lively summer atmosphere or the tranquillity of the shoulder season.
How early should I book a Chelsea holiday rental?
Book your Chelsea holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chelsea?
In Chelsea, Massachusetts, visitors can explore a variety of attractions that showcase the area's rich history and vibrant culture. The Chelsea Market Basket is a popular spot where locals and tourists alike can find fresh produce, meats, and specialty items. Just a short walk away, the Chelsea Waterfront offers scenic views of the Boston skyline and provides a lovely setting for leisurely strolls along the Mystic River.

For art enthusiasts, the Chelsea Art Walk showcases numerous galleries and studios, making it a great way to experience the local creative scene. The Chelsea Soldiers' Home, with its beautiful grounds, is a significant historical site that pays tribute to veterans and offers a glimpse into the area's past. Additionally, the nearby Revere Beach, which is a short drive away, provides a lovely beach experience for those looking to enjoy some sun and sand.
Can I change or cancel my Chelsea home rental booking on Vrbo?
To find Chelsea holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chelsea holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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