Chelsea vacation rentals

We found 2,670 vacation rentals — enter your dates for availability

Discover a selection of 21 apartments and other vacation rentals in Chelsea that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include air conditioning and a pool. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Find out more about Chelsea

Why visit Chelsea

  • Cultural Diversity: Experience Chelsea's rich blend of cultures, reflected in its diverse culinary scene and community events.
  • Urban Parks: Enjoy the city's parks, perfect for relaxation, picnics, and family outings amidst the urban landscape.
  • Historic Colleges: Discover local historic colleges, showcasing beautiful architecture and educational heritage.
  • Charming Neighborhoods: Explore friendly residential areas that offer quaint streets and a welcoming atmosphere.
  • Variety of Accommodations: Find the ideal vacation rental, from cozy homes to modern apartments, enhancing your stay.

Popular types of accommodation in Chelsea

Discover the perfect getaway in Chelsea with a variety of vacation rentals to suit your needs. From cozy houses to modern apartments and stylish condos, there’s something for everyone. Whether you’re looking for a spacious house rental or a charming one-bedroom apartment, our selection of holiday flats ensures you’ll find the ideal base for your adventures. Explore Chelsea with confidence and enjoy your stay.

  • Houses: The top choice for visitors to Chelsea, these homes offer a spacious and comfortable environment for families or groups looking to enjoy their time together.
  • Apartments: A favored option for many travelers, apartments provide a convenient and modern living space, ideal for those seeking a local experience.
  • Condos: Often chosen for their amenities, condos combine comfort with a touch of luxury, making them a great option for vacationers.
  • Cottages: Perfect for a quaint getaway, these charming retreats offer a cozy atmosphere for relaxation.
  • House Boats: For a unique experience, house boats provide a floating home with stunning views, perfect for adventurers.**

Top attractions near Chelsea

Chelsea, Massachusetts, offers a vibrant blend of city, business, and cultural experiences perfect for all types of travelers. Explore urban parks, historic colleges, and event venues that cater to families and cultural enthusiasts alike. Whether you're visiting for leisure or business, Chelsea's attractions provide a rich urban experience that highlights the best of city life.

  • Fenway Park: This historic sports stadium, located 5 miles from Chelsea, is home to the Boston Red Sox. Experience the excitement of a game in one of America's oldest ballparks, rich in sports culture and tradition.
  • TD Garden: Situated 2 miles away, this versatile event venue hosts everything from concerts to sports events. Experience the vibrant business atmosphere and catch a Boston Celtics or Bruins game while enjoying top-notch entertainment.
  • Boston Common: Just 3 miles from Chelsea, this urban park offers a beautiful outdoor space ideal for families. Enjoy leisurely strolls, picnics, and seasonal activities amidst the historic backdrop of the city.

Things to do recommended for couples

For a romantic getaway in Chelsea, catch a concert at the MGM Music Hall at Fenway, just 4 miles away, or embrace adventure at the Courageous Sailing Center, 2 miles from town. Don't miss the enchanting performances at the Jose Mateo Ballet Theatre, also 4 miles away.

Things to do recommended for families

Families visiting Chelsea can explore the fun of LEGOLAND® Discovery Center, just 2 miles away, enjoy sports at Agganis Arena, 5 miles from Chelsea, or marvel at the stars at the Charles Hayden Planetarium, located 3 miles away. Exciting adventures await.

Things to do recommended for groups

For a memorable group experience in Chelsea, visit Faneuil Hall Marketplace for shopping and entertainment, enjoy a show at the Orpheum Theater for a taste of culture, or sample craft beers at Harpoon Brewery for a fun evening out. Each spot offers a unique vibe for your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Chelsea with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Chelsea with young kids: Traveling with little ones can be quite a task. It's essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chelsea: For many families, a vacation wouldn't feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Chelsea: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Chelsea

During your visit to Chelsea, Massachusetts, immerse yourself in the vibrant city vibes and explore the charming residential areas. Just a short trip away, Downtown Brooklyn offers a bustling atmosphere, while Cobble Hill invites you to enjoy its historic streets and friendly ambiance. Consider staying in Plainview vacation rentals for a cozy experience that perfectly balances urban excitement with family-friendly appeal. Chelsea's diverse culture and warm community make it an ideal destination for every type of traveler.

  • Boston: As a vibrant metropolis, Boston is a must-visit destination located directly adjacent to Chelsea. Known for its rich history and cultural diversity, Boston offers travelers a city-themed experience that is perfect for families and culture enthusiasts alike. Visitors can enjoy an array of activities, from educational museums to lively music concerts. The city is home to iconic landmarks such as historic sports stadiums and bustling shopping centers, making it an exciting hub for both leisure and exploration.
  • Downtown Boston: Located 3 miles from Chelsea, Downtown Boston is a dynamic neighborhood that serves as the heart of the city. It attracts visitors seeking a blend of cultural and family-oriented experiences. Popular activities include shopping at numerous centers and engaging with local educational institutions. The area boasts notable attractions such as historic sports venues and event conference spaces, providing plenty of opportunities for entertainment and learning amidst the city's rich heritage.
  • Revere: Just 2 miles from Chelsea, Revere is a charming city known for its family-friendly atmosphere and cultural offerings. Visitors can enjoy a variety of activities, including educational experiences, shopping, and attending music concerts. Revere's local landmarks, such as its beautiful beaches and family-friendly parks, make it an ideal spot for relaxation and recreation. The city's close proximity to Chelsea makes it an easy and enjoyable addition to any vacation 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 cut costs on your next getaway? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash on the total booking amount. It truly benefits you to take on the role of organizer. Become a member of our One Key rewards program to enjoy exclusive savings and accumulate OneKeyCash on eligible stays. Sign up today and begin earning.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a convenient platform to plan new adventures, refine your existing arrangements, or manage your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for your ease of use. To check out Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Chelsea is a thriving riverfront community

Located just across the mighty Mystic River from bustling Boston, Chelsea is both a great base from which to explore the iconic Massachusetts metropolis, and a vibrant destination in its own right. Multicultural and densely populated, this compact city is dotted with handsome historical buildings, eclectic eateries, boutique breweries, and picturesque parks. With an extensive array of Chelsea vacation rentals to pick from, you're bound to find one to suit your needs and wants. And should you ever need a change of scenery, the cavernous museums, majestic monuments, and revered cultural venues of Boston are all just a stone's throw away.

Activities and attractions in Chelsea

Do you want to discover top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Chelsea a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • New England Aquarium (2.4 mi / 3.9 km)
  • Encore Boston Harbor (1.8 mi / 2.8 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)

Spa days and indulgent nights in Chelsea

Massachusetts boasts a thriving craft beer scene, and Chelsea is home to boutique breweries and tap rooms, where you can sample all manner of lovingly made pale ales, porters, and stouts. If you're after a more virtuous form of self-indulgence, there are also tranquil spas, where you can treat yourself to an invigorating massage, or a traditional Russian steam bath. And no visit to Chelsea is complete without an aquatic adventure or two. Take a leisurely sunset cruise around handsome Boston harbor, race down the Mystic River in your own mini speed boat, or embark on a whale-watching expedition.

Enjoy 4 distinct seasons in Chelsea

Chelsea experiences a wide range of weather conditions over the course of each year. Summer days are long, warm, and sunny, which means that Chelsea vacation rentals are in high demand between June and August. Early fall brings a crispness to the air, but temperatures usually remain pleasant until November. You'll need to wrap up warm if you're visiting in winter, although the temperature tends to hover around freezing, rather than plunge too far beneath it. Snowfall is highly variable from year to year, but certainly a common occurrence between December and February.

Exploring the natural features in Chelsea

Whether you're looking for adventure or just want to appreciate the scenery, Chelsea is a great place to spend some time outside. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • 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 (2.3 mi / 3.8 km)
  • Rose Fitzgerald Kennedy Greenway (2.4 mi / 3.9 km)
  • Charles River Esplanade (3.1 mi / 5 km)

Transportation options to and around Chelsea

The nearest airport is in Logan International Airport (BOS), located 2 mi (3.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into 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 vacation rental?
When considering a vacation rental in Chelsea, Massachusetts, the most appealing area to stay is the Chelsea Waterfront. This vibrant neighborhood not only offers stunning views of the Boston skyline but also provides easy access to numerous attractions. One of the top points of interest nearby is the Chelsea Greenway, an expansive park that invites visitors to enjoy leisurely strolls, picnics, and outdoor activities along the waterfront. Additionally, the Chelsea Market is a must-visit for food lovers, featuring a variety of local eateries and shops that showcase the city's culinary diversity.

In terms of vacation rentals, the Chelsea Waterfront area has a good selection of properties, suiting different tastes and budgets. You'll find cozy apartments with modern amenities and some with breathtaking views, making it a fantastic base for exploring both Chelsea and nearby Boston.
How much does it cost to rent a vacation home in Chelsea?
Prices for vacation 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 vacation 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, travelers should consider the waterfront areas along the nearby Revere Beach and Winthrop. Revere Beach, known for its lively boardwalk and sandy stretches, offers various rental options with amenities such as outdoor grilling areas, beachfront access, and spacious decks for enjoying the ocean breeze. Many of these properties are family-friendly, with multiple bedrooms and fully equipped kitchens, making them ideal for extended stays.

In Winthrop, just a short drive or ferry ride from downtown Boston, visitors can find charming rentals that often feature stunning views of Boston Harbor. Properties here frequently come with cozy porches, private yards, and easy access to local parks and beaches, allowing guests to enjoy outdoor activities and beachcombing.
What is the most popular type of vacation rental accomodation in Chelsea?
In Chelsea, apartments are the most popular type of vacation rental, with several options available throughout the city. These rentals typically provide a comfortable living space, fully equipped kitchens, and often include amenities such as laundry facilities and Wi-Fi, making them ideal for both short and extended stays. Additionally, several vacation houses and condos are also available, offering more spacious rooms for families or larger groups.
Are there any family house rentals in Chelsea?
In Chelsea, Massachusetts, there are several family-friendly house rentals available, making it a practical choice for those traveling with children. The neighborhood offers a variety of spacious homes that often come equipped with essential amenities like full kitchens, comfortable living areas, and outdoor spaces for kids to enjoy. Many properties are conveniently located near parks, where families can take advantage of playgrounds and green spaces.

Visitors will find that Chelsea's proximity to Boston enhances the experience, providing easy access to attractions such as the Boston Children's Museum and the New England Aquarium. The local dining scene also features family-friendly options, ensuring that mealtime is enjoyable for everyone.
Can I find long-stay vacation rentals in Chelsea?
A long-stay vacation rental in Chelsea is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chelsea?
In Chelsea, several pet-friendly house rentals are available, providing a convenient base for exploring the vibrant Boston area. Many of these homes come equipped with modern amenities such as fully stocked kitchens, comfortable living spaces, and outdoor areas where pets can play. The proximity to Boston allows easy access to attractions while enjoying the comforts of home.

Nearby, the Chelsea Greenway offers lovely walking paths great for strolls with your dog, while the surrounding parks provide additional space for outdoor activities and relaxation. Additionally, the East Boston neighborhood, just a short distance away, features parks like Piers Park, which has great views and walking trails suitable for pets.
Are there any remote work vacation rentals in Chelsea?
In Chelsea, Massachusetts, there are several vacation rentals suitable for remote work, with about 12 options available. Travelers can expect properties equipped with essential amenities for a productive stay, including high-speed Wi-Fi, dedicated office spaces, and comfortable desks with ergonomic chairs. Many rentals also feature additional conveniences like computer monitors and safes, suiting the needs of remote workers.

The location provides easy access to various points of interest, including the vibrant neighborhoods of East Boston and the nearby waterfront parks, offering opportunities for relaxation during breaks. Additionally, Chelsea's proximity to Boston allows for easy exploration of the city's rich history, dining, and entertainment options. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chelsea vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chelsea with parking available—perfect for families or travelers 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 vacation rental amenities include WiFi, kitchens equipped for cooking, blenders for preparing smoothies or other meals, coffee and tea makers for convenient morning routines, and electric kettles for quick hot water access.
When is the best time to visit Chelsea for a vacation rental?
The best time to visit Chelsea, Massachusetts, for a vacation rental is during the peak season from May to July. This vibrant period attracts travelers eager to soak in the lively atmosphere of summer, with July being the most popular month. During these months, you can enjoy a delightful mix of outdoor activities, festivals, and local events, all while experiencing the warm and inviting climate that typically ranges from the mid-60s to the low 80s Fahrenheit.

As you stroll through Chelsea, you'll find plenty of opportunities for sightseeing, from the historic Chelsea Square to the beautiful waterfront along the Chelsea River. The pleasant temperatures create ideal conditions for exploring the local parks, indulging in outdoor dining, or simply wandering through the streets to discover charming shops and art installations.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to enjoy the fall ambiance and explore the area's attractions without the summer crowds.
How early should I book a Chelsea vacation rental?
Book your Chelsea vacation 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 vacation 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 highlight the city's rich history and vibrant culture. The Chelsea Greenway offers a scenic pathway along the waterfront, ideal for walking, jogging, or biking while enjoying views of the Boston skyline across the harbor. Nearby, the Chelsea Market provides a lively atmosphere with diverse food options and local shops, making it a great spot for dining and shopping.

For a taste of local history, the Chelsea Soldier's Home features beautiful grounds and a museum dedicated to veterans, reflecting the city's commitment to honoring those who served. The Chelsea Clock Company, one of the oldest clock manufacturers in the United States, can be found in the area, where visitors can learn about its fascinating history.

Additionally, the nearby Revere Beach is a short drive away, offering a lovely sandy beach for relaxation and leisure activities.
Can I change or cancel my Chelsea home rental booking on Vrbo?
To find Chelsea vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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