Chelsea holiday lettings

We found 2,539 holiday rentals — enter your dates for availability

Discover a selection of 6 homes 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:14 Nov - 21 Nov
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Find out more about Chelsea

Find out more about Chelsea

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. TD Garden and New England Aquarium 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:

  • New England Aquarium (2.4 mi / 3.9 km)
  • Encore Boston Harbor (1.9 mi / 3 km)
  • Harpoon Brewery (3.1 mi / 5 km)
  • Boston Marathon Finish Line (3.7 mi / 6 km)
  • Samuel Adams Brewery (6.4 mi / 10.4 km)
  • Franklin Park Zoo (6.6 mi / 10.7 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 National Historical Park (1.8 mi / 2.8 km)
  • Revere Beach Reservation (2.3 mi / 3.8 km)
  • Revere Beach (2.3 mi / 3.8 km)
  • Rose Fitzgerald Kennedy Greenway (2.4 mi / 3.9 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 a holiday rental in Chelsea, Massachusetts, a popular area to stay is near Chelsea's waterfront. This vibrant neighbourhood offers a picturesque view of the Boston skyline and provides easy access to several attractions. You can explore the Chelsea Market, known for its diverse dining options and local shops, or take a leisurely stroll along the Chelsea Greenway, which offers beautiful views and is superb for walking or cycling.

Another appealing area to consider is the Chelsea Square area. Here, you'll find a mix of historic and modern architecture, along with a variety of restaurants and cafés that reflect the city's diverse culture. The Chelsea Public Library is a lovely spot for a quiet afternoon, and the nearby Chelsea Soldiers' Home offers a glimpse into the community's rich history.
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, travellers should consider the nearby coastal areas of Revere and Winthrop, which are easily accessible and offer lovely beachside properties. In Revere, the Revere Beach area is particularly popular, with a long sandy shoreline that hosts a variety of beachfront rentals. Many of these properties come equipped with amenities such as private balconies, outdoor grills, and easy beach access, making them superb for families or groups looking to enjoy the sun and surf.

In Winthrop, visitors can find charming homes along the coastline with stunning views of the Boston skyline. Many of these rentals feature spacious decks, modern kitchens, and proximity to local parks and walking trails. The area also offers a relaxed atmosphere with quaint shops and restaurants where guests can enjoy fresh seafood and other local delicacies.
What is the most popular type of holiday rental accomodation in Chelsea?
In Chelsea, apartments are the most popular type of holiday rental, with several available throughout the city. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and often include conveniences like laundry facilities and Wi-Fi. Many are situated in vibrant neighbourhoods, allowing easy access to local shops, restaurants, and parks.
Are there any family house rentals in Chelsea?
In Chelsea, Massachusetts, there are several family-friendly house rentals available, suiting those looking for spacious rooms. The neighbourhood is conveniently located near Boston, allowing visitors easy access to a wealth of attractions. Many properties in the area feature comfortable living spaces, full kitchens for family meals, and outdoor areas where children can play.
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, Massachusetts, there are several pet-friendly house rentals available that cater to those travelling with furry companions. Many of these properties feature modern amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, superb for enjoying some fresh air with your pets.
Are there any remote work holiday rentals in Chelsea?
In Chelsea, Massachusetts, there are several remote work-friendly holiday rentals available, around 14 in total. This vibrant area offers a mix of urban convenience and local charm, making it an appealing choice for remote workers. Most properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and sometimes even separate office areas, ensuring a productive environment for those working from home. 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 holiday rentals typically feature a range of amenities designed to enhance guests' comfort and convenience. Most accommodations include fully equipped kitchens for those who prefer self-catering, alongside essential appliances such as microwaves and refrigerators. Free Wi-Fi is commonly available, ensuring that guests can stay connected during their stay. Additionally, many rentals come with coffee makers, allowing visitors to enjoy a fresh brew at their leisure.
When is the best time to visit Chelsea for a holiday rental?
July is the most popular time to visit Chelsea, Massachusetts, as it falls within the peak season that runs from May to July. During these vibrant months, the area buzzes with activity, making it an ideal time for travellers seeking a lively atmosphere. Visitors can take advantage of the warm summer weather, with temperatures typically ranging from 20 to 30 degrees Celsius, superb for outdoor dining, festivals, and exploring the local culture.

The summer months offer a lot of options for sightseeing, including nearby attractions like the picturesque waterfront and charming neighbourhoods filled with shops and eateries. With an abundance of events and activities, July provides a fantastic backdrop for those looking to immerse themselves in the local scene.

If you're looking for a more budget-friendly option, consider planning your visit in November. This month allows for a quieter experience, where you can appreciate Chelsea's unique character without the hustle and bustle of peak tourist season. Take leisurely strolls through the area, enjoy the local cuisine, and perhaps discover some hidden gems.
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 several attractions that highlight the city's rich history and vibrant culture. The Chelsea Clock Company, known for its historic craftsmanship, offers insights into the local manufacturing heritage. Nearby, the Chelsea Waterfront provides picturesque views of the Boston skyline, making it a lovely spot for leisurely walks.

The Chelsea Greenway, a popular linear park, offers a pleasant space for outdoor activities, and is lined with art installations that reflect the city's creativity. Additionally, the Chelsea Market Basket is a bustling marketplace where visitors can sample local produce and baked goods. For those interested in history, the Chelsea Soldiers' Home, with its beautiful grounds, showcases the city's commitment to honouring veterans.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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