Holiday Rentals in Massachusetts

41544 available vacation rental offers

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Massachusetts holiday rentals
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Best Holiday rentals and Airbnb offers in Massachusetts

Best family friendly Massachusetts holiday rentals

Among the 41544 accommodations in Massachusetts, here are the 4 best family friendly rentals

Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking - Massachusetts
9.4 79 reviews
Massachusetts
27/06 – 04/07
SG$604/nighttotal: SG$4228 (7 )

Unique & Peaceful Boston Home, Ideal For 2026 World Cup Visitor, Free Parking

2 2
apartment , Boston
This apartment is located in a tranquil neighbourhood in Boston, just 10km from the Boston Museum of Fine Arts and 11km from Fenway Park. It has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is a spacious two-bedroom property with one bathroom, covering 88 square metres and comfortably accommodating up to five guests. It offers a range of amenities including a fully equipped kitchen, private garden, free parking, and a washing machine, making it ideal for families or groups of friends exploring Boston.
Stylish 1br In Assembly Square | Pool, Gym & Views - Massachusetts
10 3 reviews
Massachusetts
01/08 – 30/09
SG$385/nighttotal: SG$23100 (60 )

Stylish 1br In Assembly Square | Pool, Gym & Views

5 2
apartment , Somerville
This Somerville flat is situated in the centre, a 5-minute walk from Assembly Row and LEGOLAND Discovery Centre, with Assembly Station just 200 metres away for excellent public transport links.
This 56 square metre dwelling offers accommodation for up to 4 guests, featuring 5 bedrooms, a fully equipped kitchen, air conditioning, a swimming pool, a garden, and a pool table for entertainment.
Great Space To Be Together And Spread Out - Massachusetts
10 2 reviews
Massachusetts
01/09 – 28/02
SG$192/nighttotal: SG$34560 (180 )

Great Space To Be Together And Spread Out

3 1
apartment , Hamilton
This three-bedroom holiday home in South Hamilton, Massachusetts, is situated a short drive (approximately 43km) from both Wingaersheek and Good Harbor beaches, and around 26km from Salem's Witch Museum and Castle Hill on the Crane Estate.
The property offers internet, air conditioning, a dryer and ironing board; sleeping five guests comfortably, with essential toiletries provided.
New! Family-friendly Getaway -1 Mi To Dtwn Salem W Roof Deck & Tiki Bar - Massachusetts
9.7 219 reviews
Massachusetts
03/07 – 05/07
SG$1366/nighttotal: SG$2732 (2 )

New! Family-friendly Getaway -1 Mi To Dtwn Salem W Roof Deck & Tiki Bar

4 12
apartment , Salem
This family-friendly apartment in Salem is conveniently located within walking distance of the downtown area, placing you close to shops, restaurants, and attractions like the Peabody Essex Museum and The House of the Seven Gables. The property has received excellent ratings for location, cleanliness, and overall experience.
The three-bedroom apartment offers ample space for up to 12 guests across its 1000 square metres. You'll enjoy modern amenities such as a fully equipped kitchen, air conditioning, a private garden, and a swimming pool, ensuring a comfortable and enjoyable stay.

Top cities

Best pet friendly Massachusetts holiday rentals

Among the 41544 accommodations in Massachusetts, here are the 4 best pet friendly rentals

Brand-new & Modern 2 Bedrooms And 1.5 Baths Apt. - Massachusetts
9.8 7 reviews
Massachusetts
25/07 – 01/08
SG$250/nighttotal: SG$1750 (7 )

Brand-new & Modern 2 Bedrooms And 1.5 Baths Apt.

2 2
apartment , Worcester
This two-bedroom flat in Worcester is conveniently located a 5-minute drive from John J. Binienda Memorial Beach and 3 minutes from the Blackstone River, with Fitton Field a 12 to 13-minute walk away.
This 103 square meter apartment accommodates up to four guests and includes internet, air conditioning, laundry facilities, and is close to cultural attractions such as The Hanover Theatre for the Performing Arts and the Worcester Historical Museum.
Upscale Penthouse With Gym Parking Near Mgh Tufts - Massachusetts
9.8 5 reviews
Massachusetts
12/08 – 14/08
SG$839/nighttotal: SG$1678 (2 )

Upscale Penthouse With Gym Parking Near Mgh Tufts

1 5
apartment , Boston
This upscale penthouse apartment is located near Boston's South Station, a short walk from Back Bay and major attractions such as the Freedom Trail, less than 1.6km from Custom House.
The 70 square metre dwelling boasts one bedroom, one bathroom, sleeps seven guests, includes parking, a gym, and a fully equipped kitchen.
Hawley Home W\/ Deck: 4 Mi To Berkshire East Resort - Massachusetts
9.4 23 reviews
Massachusetts
13/07 – 19/07
SG$274/nighttotal: SG$1644 (6 )

Hawley Home W\/ Deck: 4 Mi To Berkshire East Resort

1 2
resort , Hawley
This Charlemont holiday home, offered as 'Hawley Home W/ Deck: 4 Mi To Berkshire East Resort', is situated approximately 4.3km from Berkshire East and close to the Mohawk Trail State Forest (4.3km) and Deerfield River (4.7km).
The 69 square metre property boasts two bedrooms, one bathroom, sleeps three guests, and includes a patio, tennis court access, and Wi-Fi; nearby activities include Swift River and Zoar Outdoor/Deerfield Valley Canopy Tours (within 9.7km).
Charming 2 Bedroom Townhome W/private Office Suite - Massachusetts
9.5 77 reviews
Massachusetts
03/07 – 15/07
SG$369/nighttotal: SG$4428 (12 )

Charming 2 Bedroom Townhome W/private Office Suite

1 4
house , Woburn
This Woburn townhome, a New England Colonial-style property, enjoys a convenient location near Interstates 95 and 93, providing easy access to Boston (under 32km) and local amenities.
The two-bedroom, one-bathroom house sleeps six, features a fully equipped kitchen including a dishwasher, offers parking for up to three cars, and boasts high-speed internet; nearby restaurants and hospitals are within walking distance.

Frequently asked questions about holiday rentals in Massachusetts

  • What are the must-see sights in Massachusetts?

    For must-see sights in Massachusetts, you've got plenty of options! In Boston, you absolutely have to visit the Freedom Trail, a 4-kilometre-long path that takes you past 16 historical landmarks like the Boston Common, Paul Revere's House, and the Old North Church. Then there's Plymouth, with Plymouth Rock and Plimoth Patuxet Museums, offering a glimpse into the early days of the colony. Further afield, Salem's Witch Museum and historical sites are fascinating, and the Berkshires offer stunning natural beauty and cultural attractions like Tanglewood.
  • What are the best Airbnb and vacation rentals in Massachusetts?

    Near Boston Historic Two-bedroom With Modern Amenities, Luxurious Renovated House and Your Home For The Holidays are the most popular Airbnb and vacation rentals in Massachusetts among travelers.

  • Are there unique natural phenomena in Massachusetts?

    Massachusetts boasts some interesting natural features. The dramatic cliffs and coastline of the North Shore are a highlight, particularly around Gloucester and Rockport. The Berkshires offer stunning mountain scenery, perfect for hiking and exploring. While not a unique phenomenon globally, the autumn foliage in the state is spectacular and draws many visitors.
  • What are the most popular Airbnbs in Massachusetts?

  • What essentials should you bring along for a trip to Massachusetts?

    Pack for all types of weather! Massachusetts can experience varied conditions, even within a single day. Comfortable walking shoes are a must, as you'll likely be doing a lot of exploring on foot. Layers of clothing are essential, including a waterproof jacket. Don't forget sunscreen, a hat, and sunglasses, especially during the summer months. A reusable water bottle is also highly recommended.
  • What are the best vacation rentals with a pool in Massachusetts?

  • What famous events or festivals are happening in Massachusetts?

    The Boston Marathon is a world-famous event held annually in April. In the summer, the Boston Harborfest celebrates the city's maritime history with various events. The state also hosts numerous local town fairs and festivals throughout the year, many celebrating harvests and local traditions. Specific dates vary, so checking local listings closer to your travel dates is advisable.
  • What are the best rentals for families and kids in Massachusetts?

  • Where can you find the best restaurants serving local dishes in Massachusetts, and what are the must-try specialties?

    For classic New England fare, look for restaurants in Boston's North End for excellent Italian-American food. Seafood is a staple, and you'll find many fantastic restaurants along the coast serving fresh catches. Try clam chowder (a creamy soup with clams), lobster rolls (lobster meat in a toasted bun), and Boston baked beans (slow-cooked beans in molasses). Many restaurants throughout the state offer regional variations on these dishes.
  • What are the best rentals or Airbnbs with a jacuzzi in Massachusetts?

  • What are some less-famous attractions in Massachusetts that are worth a visit?

    Consider exploring the charming towns of the Berkshires, like Lenox and Stockbridge, offering beautiful scenery and quaint shops. The Plimoth Patuxet Museums, while known, often get overlooked in favour of Plymouth Rock. The Arnold Arboretum in Boston is a beautiful botanical garden with a vast collection of trees and plants. The Cape Cod National Seashore offers stunning beaches and hiking trails beyond the usual tourist hotspots.
  • What are the best activities for engaging with locals and understanding their culture in Massachusetts?

    Visiting local farmers' markets is a great way to interact with residents and sample regional produce. Attending a local event or festival can provide insights into community life. Striking up conversations with people in smaller towns and villages can lead to interesting interactions. Exploring local pubs and restaurants offers opportunities to experience the social side of Massachusetts culture.
  • What unique natural landscapes and terrain features can travellers explore in Massachusetts?

    Massachusetts has a diverse landscape. The coastline offers dramatic cliffs, sandy beaches, and rocky inlets. The Berkshires provide mountainous terrain perfect for hiking and exploring. Cape Cod's unique geography, a long, narrow peninsula, provides a distinct coastal experience. The state's many islands, such as Martha's Vineyard and Nantucket, offer unique natural beauty and wildlife.
  • How many days are ideal for a trip to Massachusetts, and what are some itinerary suggestions?

    The ideal length of stay depends on your interests. A long weekend (3-4 days) allows for exploring Boston and its surroundings. A week (7 days) enables a more in-depth exploration of Boston, a day trip to Salem, and perhaps a visit to Cape Cod or the Berkshires. Two weeks or more would allow for a more relaxed pace and exploration of more remote areas.

Nearby regions

Best Massachusetts holiday rentals with a pool

Among the 41544 accommodations in Massachusetts, here are the 4 best rentals with a pool

The Clearing - Quiet - Close To Nature - Massachusetts
10 214 reviews
Massachusetts
07/01 – 12/01
SG$246/nighttotal: SG$1230 (5 )

The Clearing - Quiet - Close To Nature

1 2
cottage , Chesterfield
This Chesterfield cottage, situated 0.3km from the Westfield River and 4.8km from the Chesterfield Gorge Reservation, offers easy access to hiking trails and scenic walks.
This 65 square metre self-catering holiday home sleeps four, boasting two bedrooms, one bathroom, a private pool, barbecue, fireplace, and free Wi-Fi.
Family Fun In Boston Rooftop Pool & City Views - Massachusetts
Massachusetts
16/07 – 18/07
SG$1201/nighttotal: SG$2402 (2 )

Family Fun In Boston Rooftop Pool & City Views

1 3
apartment , Boston
This Boston flat offers a prime location, a 14-minute walk from the Freedom Trail and 1448 meters from Boston Common, placing it within easy reach of historic sites such as the Old State House and King's Chapel.
This 70 square meter residence accommodates up to 9 guests, featuring a separate bedroom, a living room with a fireplace, a fully equipped kitchen with a dishwasher and oven, a rooftop swimming pool, a fitness centre, and on-site casino, with free Wi-Fi and nearby cycling and water park activities.
Pool+hottub+pickleball+game+movie+playroom+petsok - Massachusetts
Massachusetts
26/06 – 03/08
SG$2850/nighttotal: SG$108300 (38 )

Pool+hottub+pickleball+game+movie+playroom+petsok

1 5
apartment , Barnstable Town
This Hyannis flat is located in Barnstable Town, offering easy access to Hyannis Harbour, Main Street Hyannis, and beaches such as Kalmus and Craigville within a 15-minute drive.
This spacious property accommodates up to 14 guests and boasts a private pool with a volleyball net, a hot tub, a pickleball court, a games room, a cinema, a children's playroom, and an outdoor dining area with a fire pit and BBQ.
Relax & Renew At Luxury Villa With Heated Pool & Hot Tub,tennis,bikes,firepit! - Massachusetts
9.2 27 reviews
Massachusetts
11/09 – 13/09
SG$2947/nighttotal: SG$5894 (2 )

Relax & Renew At Luxury Villa With Heated Pool & Hot Tub,tennis,bikes,firepit!

5 2
apartment , Oak Bluffs
This family-friendly holiday home is located in Oak Bluffs, just a short distance from the beach, Circuit Avenue, and other local attractions. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious 4-bedroom property spans 223 square metres and features a range of amenities including a private pool, a Jacuzzi, a tennis court, and a barbecue grill. Guests can enjoy the beautiful weather in the private garden or relax in the comfortable living spaces.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

2 Mi To Waterfront: Walkable Fall River Apartment! - Massachusetts
Massachusetts
27/06 – 04/07
SG$201/nighttotal: SG$1407 (7 )

2 Mi To Waterfront: Walkable Fall River Apartment!

2 2
apartment , Fall River
This pet-friendly Fall River flat is conveniently located near basketball courts, a 1.9km drive from the Lizzie Borden Bed and Breakfast, and a 2.2km walk from the Fall River Historical Society Museum.
The 84 square metre self-catering apartment sleeps four, boasting two bedrooms, one bathroom, a fully equipped kitchen (including fridge, microwave, dishwasher, and stove), internet access, on-site parking, and proximity to attractions such as Battleship Cove and the USS Massachusetts Battleship Museum.
"A Cozy Place At Fieldstone Beach" - Massachusetts
9.6 86 reviews
Massachusetts
04/10 – 31/10
SG$355/nighttotal: SG$9585 (27 )

"A Cozy Place At Fieldstone Beach"

2 2
apartment , Marshfield
This charming apartment is located just 300 feet from the beach in Marshfield, offering easy access to the beautiful coastline. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is well-equipped with a kitchen, laundry room, and a private backyard with a fire pit. Guests can enjoy the private beach access, outdoor shower, and the porch/deck with a picnic table.
Fearlessrose Vacation Rental 198 - Massachusetts
9.1 8 reviews
Massachusetts
18/07 – 19/07
SG$458/nightfor 1 night

Fearlessrose Vacation Rental 198

4 2
apartment , Springfield
This newly renovated one-bedroom flat is conveniently located in Springfield, just a short drive from The Big E and the Eastern States Expo Center. The surrounding area offers easy access to local attractions and amenities.
The flat comfortably sleeps up to eight guests and features a fully equipped kitchen, private parking, and complimentary Wi-Fi. Guests can also enjoy the convenience of an on-site coffee shop, car rental service, and a non-smoking environment.
Quincy Beach Home Next To Boston & T, Free Parking - Massachusetts
10 184 reviews
Massachusetts
01/09 – 28/02
SG$317/nighttotal: SG$57060 (180 )

Quincy Beach Home Next To Boston & T, Free Parking

3 1
apartment , Quincy
This three-bedroom apartment in Quincy is ideally located within a 10km radius of attractions such as Granite Links Golf Club, the University of Massachusetts Boston, and the John F. Kennedy Presidential Library and Museum. It has received excellent ratings for location, cleanliness and user experience.
This spacious home is perfect for families or groups of up to six people, and includes a fully equipped kitchen, a private yard, a furnished patio, and a garden with barbecue grills.
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