Chelsea holiday rentals

We found 2,779 holiday rentals — enter your dates for availability
Discover a selection of 5 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:29 Jan - 5 Feb

View of Spinnaker Island and water from Master Bedroom Suite
Excellent
(49 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

8% off
AU$2,708
for 7 nights, 1 room
AU$387 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Living Room, 65" Smart TV, Crate&Barrel Sofas, Bookshelf & Cabinet
Exceptional
(8 reviews)

Premium Loft 3BR&2BA • Heart of Downtown Boston • Walkable to Sights

Boston

8% off
AU$6,130
for 7 nights, 1 apartment
AU$876 per night
includes taxes & fees
Premium Loft 3BR&2BA • Heart of Downtown Boston • Walkable to Sights
Private kitchen
Exceptional
(35 reviews)

Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH

Boston

8% off
AU$9,261
for 7 nights, 1 apartment
AU$1,323 per night
includes taxes & fees
Beacon Hill Penthouse, Stately 2-bedroom apartment with AC, WiFi near MGH
Exterior detail
Exceptional
(6 reviews)

Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17

Newton

9% off
AU$25,595
for 7 nights, 1 home
AU$3,656 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Marina
Exceptional
(100 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,927
for 7 nights, 1 room
AU$418 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Living room, 65" Smart TV, Genuine leather sectional sofa, Book and toys shelf.
Exceptional
(70 reviews)

Spacious Sunlit 3BR • Best Location of Downtown Boston • Family Favorite

Boston

8% off
AU$4,977
for 7 nights, 1 apartment
AU$711 per night
includes taxes & fees
Spacious Sunlit 3BR • Best Location of Downtown Boston • Family Favorite
Living area
Wonderful
(21 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
AU$5,860
for 7 nights, 1 apartment
AU$837 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Dining
Exceptional
(98 reviews)

The Inn at Newton Highlands, boutique apartment-hotel

Newton

12% off
AU$4,106
for 7 nights, 1 room
AU$587 per night
includes taxes & fees
The Inn at Newton Highlands, boutique apartment-hotel
Interior
Exceptional
(51 reviews)

The Inn at Newton Highlands, Suite 2, Apartment-Hotel

Newton

8% off
AU$5,172
for 7 nights, 1 apartment
AU$739 per night
includes taxes & fees
The Inn at Newton Highlands, Suite 2, Apartment-Hotel
Living area
Exceptional
(16 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
AU$9,403
for 7 nights, 1 home
AU$1,343 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Room
Exceptional
(5 reviews)

Family-Friendly 3BR Apartment Close to Everything

Boston

8% off
AU$3,041
for 7 nights, 1 apartment
AU$434 per night
includes taxes & fees
Family-Friendly 3BR Apartment Close to Everything
Interior
Excellent
(7 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
AU$7,044
for 7 nights, 1 apartment
AU$1,006 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,952
for 7 nights, 1 home
AU$850 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Dining
Exceptional
(37 reviews)

**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!

Boston

8% off
AU$6,994
for 7 nights, 1 apartment
AU$999 per night
includes taxes & fees
**Fresh** Modern Triplex in a Classic Boston Row House, Amazing City Views!
Room
Exceptional
(83 reviews)

The Inn at Newton Highlands, boutique apartment-hotel

Newton

12% off
AU$3,801
for 7 nights, 1 apartment
AU$543 per night
includes taxes & fees
The Inn at Newton Highlands, boutique apartment-hotel
Property grounds
Exceptional
(24 reviews)

Charming 2-bedroom house with a hidden garden in lovely Cambridge.

Cambridge

8% off
AU$4,993
for 7 nights, 1 home
AU$713 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Interior
Exceptional
(29 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,648
for 7 nights, 1 apartment
AU$807 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Room
Exceptional
(82 reviews)

The Pistachio Room at TPH - Boston

Boston

7% off
AU$1,421
for 7 nights, 1 room
AU$203 per night
includes taxes & fees
The Pistachio Room at TPH - Boston
Path to yard in July
Exceptional
(152 reviews)

Maria's JP Rental - Boston Duplex in Popular Jamaica Plain "JP" area

Boston

9% off
AU$2,577
for 7 nights, 1 apartment
AU$368 per night
includes taxes & fees
Maria's JP Rental - Boston Duplex in Popular Jamaica Plain "JP" area
Living area
Exceptional
(12 reviews)

Comfy, Stylish Apt. Near Uni's, Driveway

Somerville

12% off
AU$6,734
for 7 nights, 1 apartment
AU$962 per night
includes taxes & fees
Comfy, Stylish Apt. Near Uni's, Driveway
Living area
Wonderful
(13 reviews)

Boston Spacious Apartment with private outdoor patio

Boston

5% off
AU$5,988
for 7 nights, 1 apartment
AU$855 per night
includes taxes & fees
Boston Spacious Apartment with private outdoor patio
Dining
Excellent
(18 reviews)

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

Medford

7% off
AU$2,837
for 7 nights, 1 home
AU$405 per night
includes taxes & fees
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking
Cool Historic Details in this 1860's townhome apartment, stairs required!
Exceptional
(47 reviews)

Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!

Boston

8% off
AU$6,994
for 7 nights, 1 apartment
AU$999 per night
includes taxes & fees
Fort Hill Inn- Modern City Triplex !**L@@K **Minutes to Center! With Parking!
Dining
Excellent
(11 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
AU$5,088
for 7 nights, 1 apartment
AU$727 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • LEGO® Discovery Center Boston (2.4 mi / 3.9 km)
  • New England Aquarium (2.4 mi / 3.9 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)

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)
  • 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)

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.
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.
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 Stayz.
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.
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.
Are all fees included in the Chelsea holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chelsea holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Chelsea holiday homes?
You can find great discounts on holiday homes in Chelsea on Stayz, 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.
Can I change or cancel my Chelsea holiday home booking on Stayz?
To find Chelsea holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chelsea?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Chelsea holiday home?
Book your Chelsea holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chelsea?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chelsea to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.