Holiday Rentals in Massachusetts

61432 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Massachusetts holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Massachusetts

Best family friendly Massachusetts holiday rentals

Among the 61432 accommodations in Massachusetts, here are the 4 best family friendly rentals

Cozy, 3br Lake-side Retreat And Outdoor Oasis - Massachusetts
9.7 68 reviews

Cozy, 3br Lake-side Retreat And Outdoor Oasis

apartment, Dudley
This charming cottage is located in Dudley, Massachusetts, just a short drive from major highways, offering easy access to the area while still feeling secluded. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The cottage is designed with an open layout, connecting the kitchen, living room, and dining areas, and comfortably sleeps up to five guests. The property offers a range of amenities and activities, including a private beach, a large backyard with a fire pit and picnic table, and access to kayaks, paddleboards, and a canoe for exploring the lake.
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat - Massachusetts
9.8 128 reviews

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

apartment, Gloucester
This charming apartment is situated between the picturesque Annisquam Village and Lanesville, just a short walk from Plum Cove Beach and the Greenbelt hiking trails, and less than 2km from Halibut Point in Rockport. It boasts excellent user ratings and is perfect for families and pet owners.
The apartment has three bedrooms and one bathroom, covering a comfortable 116 square metres and accommodating up to six guests. You'll find a fully equipped kitchen, a garden, parking, and a jacuzzi, making it ideal for a relaxing stay with plenty of options for outdoor activities.
Updated England Victorian X Modern 5 Br, 2.5 Ba - Massachusetts
10 15 reviews

Updated England Victorian X Modern 5 Br, 2.5 Ba

apartment, Quincy
This spacious five-bedroom flat in Quincy offers convenient walking distance to the MBTA train station, facilitating effortless commutes to Boston, and is situated near a variety of local eateries.
This family-friendly accommodation sleeps up to eight guests, featuring a newly updated kitchen, air conditioning, private parking for three vehicles including a Tesla charger, and on-site laundry facilities.
Luxury Spacious 2br  King & Queen Beds  2 Baths - Massachusetts
9.5 137 reviews

Luxury Spacious 2br King & Queen Beds 2 Baths

apartment, Shrewsbury
This comfortable home is situated in a pleasant neighbourhood in Shrewsbury, just a short distance from Dean Park and with convenient access to local amenities. The property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The two-bedroom house comfortably accommodates up to four guests and features a well-equipped kitchen, a spacious garden, and private parking. You can enjoy a relaxing stay with amenities such as air conditioning, high-speed Wi-Fi, and entertainment options including a Roku TV and Netflix.

Top cities

Best pet friendly Massachusetts holiday rentals

Among the 61432 accommodations in Massachusetts, here are the 4 best pet friendly rentals

Central Boston 2br Retreat Near Harvard & Transit - Massachusetts
No reviews

Central Boston 2br Retreat Near Harvard & Transit

apartment, Boston
This Central Boston flat is located 1.4 kilometres from Harvard Square and 1.4 kilometres from Harvard University, offering convenient access to Cambridge's academic centres.
This 76 square metre flat accommodates up to 9 guests, featuring 2 bedrooms, 1 bathroom, a fully equipped kitchen with a dishwasher and microwave, air conditioning, and access to a communal garden and fitness centre.
A Beautiful "Wee " Place By The Sea In Rockport - Massachusetts
8.6 45 reviews

A Beautiful "Wee " Place By The Sea In Rockport

cottage, Rockport
This Rockport holiday home is centrally located, within a 15-minute walk of Cape Ann, Thatcher Island, and the Thatcher Island National Wildlife Refuge, and under 2km from Pebble Beach and Cape Hedge Beach.
This 48 square metre self-catering property sleeps five, boasting two bedrooms, one bathroom, a fully equipped kitchenette, private patio, garden access, and barbecue facilities.
Designer 2br With Sage Kitchen & Quartz Counters - Massachusetts
10 7 reviews

Designer 2br With Sage Kitchen & Quartz Counters

apartment, Kingston
This completely renovated flat is located in historic Kingston, a short distance from local boutiques, waterfront dining, and the Kingston commuter rail, offering convenient access to the town centre and transport links.
This two-bedroom, one-bathroom apartment accommodates up to three guests and features a chef's kitchen with stainless steel appliances, high-speed Wi-Fi, air conditioning, and dedicated off-street parking, providing a spa-like atmosphere with a 'Green & White' aesthetic.
2 Bedroom Pet-friendly Apt Steps To The Beach - Massachusetts
9.6 207 reviews

2 Bedroom Pet-friendly Apt Steps To The Beach

apartment, Salisbury
This family-friendly apartment is located in Salisbury, a short distance from the beautiful beaches of Salisbury Beach State Reservation, Salisbury Beach, and Seabrook Beach. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms, a bathroom, and a living area, providing ample space for up to six guests. It also offers a range of amenities including a fully equipped kitchen, air conditioning, a swimming pool, and a terrace, ensuring a comfortable and enjoyable stay.

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 61432 accommodations in Massachusetts, here are the 4 best rentals with a pool

Quaint Beach House With Ac, Pool, Hot Tub Area, Fire Pit, And Ocean Views - Massachusetts
9.4 3 reviews

Quaint Beach House With Ac, Pool, Hot Tub Area, Fire Pit, And Ocean Views

apartment, Mashpee
This Mashpee seaside property is less than 2km from South Cape Beach, South Cape Beach State Park, and Popponesset Beach, and 3.6km from the Cape Cod Children's Museum.
Sleeping 12 guests, this six-bedroom, five-bathroom house boasts a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and barbecue facilities, perfect for families or large groups enjoying nearby beaches.
1 Bdrm Garden Apt. Villa Setting, Ctrl Worcester/boston, Ellen Elizabeth Est. - Massachusetts
8.8 6 reviews

1 Bdrm Garden Apt. Villa Setting, Ctrl Worcester/boston, Ellen Elizabeth Est.

apartment, Millbury
This Millbury flat offers a unique open-concept one-bedroom, one-bathroom layout with a New England aesthetic, situated within walking distance of the Blackstone River trail and a short drive from the Elm Draught House Cinema and The Hanover Theatre for the Performing Arts.
This 74 square meter apartment, accommodating up to two guests, features a kitchen with a fridge and microwave, air conditioning, a swimming pool, garden, spa, and parking, with nearby attractions including the Goddard Rocket Launching Site and opportunities for wildlife observation.
Walkable Area! Historic 2-home Worcester Retreat - Massachusetts
No reviews

Walkable Area! Historic 2-home Worcester Retreat

house, Worcester
This historic two-home retreat in Worcester is located in a walkable district, 15 minutes on foot from the DCU Center Arena & Convention Centre and less than 965 metres from Worcester Polytechnic Institute.
This property offers 269 square metres of living space with four bedrooms and four bathrooms, accommodating up to 15 guests with amenities including air conditioning, a swimming pool, a hot tub, a terrace, a garden, and on-site private parking.
2 Queen Beds - Massachusetts
No reviews

2 Queen Beds

apartment, Danvers
This apartment in Danvers, Massachusetts, is centrally located on Boston's North Shore, offering easy access to regional attractions, with the Peabody Museum of Natural History and the Salem Witch Museum less than 9.7 kilometres away, and Boston Harbour and downtown Boston a short drive.
This pet-friendly accommodation provides a heated indoor swimming pool, air conditioning, and complimentary basic WiFi, featuring a ground floor bedroom with two queen-sized beds, a microwave, and a fridge, suitable for up to four guests across its 19 square metres.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Cozy Condo In Bradford/haverhill Near To Boston - Massachusetts
10 27 reviews

Cozy Condo In Bradford/haverhill Near To Boston

apartment, Haverhill
This Bradford, MA flat offers convenient access to Boston via the Bradford Commuter Rail, a 10-minute walk away, and is also a short distance from downtown Haverhill's dining options.
This two-bedroom flat accommodates up to four guests and features air conditioning, a garden, parking, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, with nearby access to Bradford Ski Area and New Hampshire's scenic attractions.
Steps From Short Beach - Nahant - 3 Bedroom - Massachusetts
9.9 158 reviews

Steps From Short Beach - Nahant - 3 Bedroom

apartment, Nahant
This apartment is located in Nahant, just a short walk from Short Beach and Doggy Beach, offering views of Boston's skyline and a peaceful, coastal escape. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment is a spacious three-bedroom property with one bathroom, comfortably accommodating up to six guests. It features a fully equipped kitchen, air conditioning, a garden, and parking, making it a perfect choice for families or groups looking for a relaxing and comfortable stay.
Cozy Getaway - 10 Miles To Mount Wachusett Skiing! - Massachusetts
9.7 29 reviews

Cozy Getaway - 10 Miles To Mount Wachusett Skiing!

apartment, Leominster
This one-bedroom flat is located in Leominster, a short drive from Mount Wachusett, Tower Hill Botanic Garden, and Nashoba Valley, offering easy access to outdoor activities and attractions. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The 84 square metre flat comfortably accommodates up to four guests and features a fully equipped kitchen with a dishwasher, a washing machine, and free Wi-Fi. Enjoy the peaceful atmosphere of Leominster, relax in the garden, and take advantage of the convenient parking.
Steps To Cape Cod Canal: Pet-friendly Home - Massachusetts
9.1 136 reviews

Steps To Cape Cod Canal: Pet-friendly Home

house, Wareham
This charming house is situated in Buzzards Bay, just a short drive from Wareham, and is conveniently located within 10 miles of both Heritage Museums & Gardens and Sandwich Glass Museum. The property has received very good user ratings and excellent ratings for both location and cleanliness.
The house offers two bedrooms and one bathroom, providing comfortable accommodation for up to six guests across 121 square metres. Guests can enjoy a fully equipped kitchen, a relaxing garden with stunning sea views, and a range of amenities including air conditioning, free Wi-Fi, and parking.
©2026 cozycozy.com