Holiday Rentals in Massachusetts

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

Luxury Grand Oasis | Pool · Gym · Parking · 2br - Massachusetts
9.9 123 reviews

Luxury Grand Oasis | Pool · Gym · Parking · 2br

apartment, Everett
This Everett apartment, situated in the Commercial Triangle, offers easy access to Boston city centre via the Silver Line and Route 1.
The two-bedroom, one-bathroom flat sleeps six guests and boasts resort-style amenities including a swimming pool, fitness centre, and secure parking, plus modern kitchen and luxurious bedrooms with smart TVs.
Stylish 1br In Assembly Square | Pool, Gym & Views - Massachusetts
10 5 reviews

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

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.
Beach, Marina, Restaurants! 1 Bedroom, Living Room, Bath With Private Entrance! - Massachusetts
9.8 12 reviews

Beach, Marina, Restaurants! 1 Bedroom, Living Room, Bath With Private Entrance!

apartment, Wareham
This Wareham seaside apartment offers stunning ocean views, situated within 3km of Onset Beach, Shell Point Beach, and the Porter Thermometer Museum.
The 51-square-metre self-catering flat sleeps four, boasting a kitchen with fridge and microwave, air conditioning, a swimming pool, spa, parking, and free Wi-Fi; nearby attractions include the National Marine Life Centre and Lyman Reserve (within 5km).
Onset Beach, Cape Code.private Waterfront  Cottage - Massachusetts
9.6 209 reviews

Onset Beach, Cape Code.private Waterfront Cottage

apartment, Wareham
This charming waterfront cottage is located in Wareham, just a short drive from Tobey Hospital, Swifts Beach, Water Wizz, and Lyman Reserve, offering easy access to attractions and activities. The cottage has consistently received excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom cottage provides comfortable accommodation for up to four guests, with a spacious 74 square meters of living space. Enjoy a range of amenities including a private pool, a terrace, a garden, and free Wi-Fi, perfect for relaxing and enjoying the beautiful surroundings.

Top cities

Best pet friendly Massachusetts holiday rentals

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

Cozy Studio Suite W/ Full Kitchen Near Minute Man Historical Park - Massachusetts
No reviews

Cozy Studio Suite W/ Full Kitchen Near Minute Man Historical Park

studio, Waltham
This studio apartment is situated in downtown Waltham, directly on the lake, offering convenient access to major attractions such as Fenway Park, Tufts University, Encore Boston Harbor, and TD Garden, with wildlife viewing opportunities nearby.
This pet-friendly accommodation for four guests features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a balcony with lake views, complimentary breakfast, and on-site fitness facilities, with free Wi-Fi throughout.
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.
Walk Everywhere - Seaport, North End, Beacon Hill.  Steps From Mbta Public Transit.  Keyless Entry! - Massachusetts
9.0 2 reviews

Walk Everywhere - Seaport, North End, Beacon Hill. Steps From Mbta Public Transit. Keyless Entry!

apartment, Boston
This professionally designed, one-bedroom flat is located downtown Boston, just 500 metres from Boston Harbour and the Flynn Cruiseport, with Boston Common also within easy reach.
This apartment offers accommodation for up to four guests with the use of an air mattress and linens for an additional fee, and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, along with air conditioning and parking.
3 Mi To Onset Beach & Village! Pet-friendly Apt - Massachusetts
No reviews

3 Mi To Onset Beach & Village! Pet-friendly Apt

apartment, Wareham
This Wareham flat is situated within 5 kilometres of Water Wizz, Tobey Hospital, and Onset Beach, with Cape Cod Beaches and Onset Bay Centre also within 10 kilometres.
This pet-friendly apartment offers air conditioning, complimentary WiFi in common areas, and a kitchen equipped with a microwave oven, ensuring a comfortable stay with convenient access to seaside activities and local amenities.

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

The Island Inn On Martha's Vineyard - Massachusetts
8.4 53 reviews

The Island Inn On Martha's Vineyard

resort, Oak Bluffs
The Island Inn on Martha's Vineyard, a resort in Oak Bluffs, is located less than 2 kilometres from Joseph Sylvia State Beach, Inkwell Beach, and Seaview Beach, with Oceanographic Park and Circuit Avenue also within 3 kilometres.
This establishment offers a seasonal swimming pool, outdoor tennis courts, barbecue grills, complimentary Wi-Fi in common areas, and free on-site parking, with a complimentary shuttle service to the beach.
1 Full Bed  Ada/tub - Massachusetts
No reviews

1 Full Bed Ada/tub

apartment, Leominster
This Leominster motel offers a convenient base, located 21 kilometres from Wachusett Mountain Ski Area and 10 kilometres from Fort Devans.
This one-bedroom apartment, suitable for two guests, provides 19 square metres of living space with air conditioning, complimentary Wi-Fi, cable TV, and on-site laundry facilities, alongside access to an outdoor swimming pool.
Gorg 6ksf W Lrg Pool, Sleeps 12, 4.5 Baths, Rec Room W Bar, Pool Table & Gym. - Massachusetts
10 27 reviews

Gorg 6ksf W Lrg Pool, Sleeps 12, 4.5 Baths, Rec Room W Bar, Pool Table & Gym.

apartment, Walpole
This Walpole house is situated in a peaceful rural setting, just a short drive from Medfield Rhododendrons, Legacy Place, and Moose Hill Wildlife Sanctuary. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This spacious four-bedroom home, with a floor area of 567 square metres, comfortably accommodates up to 12 guests. The house offers a range of amenities to ensure a comfortable stay, including a private pool, a fitness centre, a tennis court, and a fully equipped kitchen.
Mansion With Heated Pool Near Ocean - Massachusetts
9.8 41 reviews

Mansion With Heated Pool Near Ocean

apartment, Plymouth
This five-bedroom house is located just 3.2 kilometres from Ellisville Harbor State Park and 4.2 kilometres from Manomet Beach, offering a peaceful and scenic setting close to the coast. Guests have consistently rated the property excellent for its location, cleanliness, and overall experience.
The 360 square metre property comfortably accommodates up to 12 guests and features a fully equipped kitchen, a private garden, a terrace, a swimming pool, a fitness centre, and parking. Guests can enjoy al fresco dining with the barbecue facilities, relax by the fireplace, or take advantage of the nearby attractions such as Pinehills Golf Club and White Horse Beach.

Neighborhoods and points of interest in Massachusetts

Best Massachusetts holiday rentals with parking

Warham Beach House - Massachusetts
9.0 9 reviews

Warham Beach House

house, Wareham
Wareham Beach House enjoys direct beach access in Wareham, Massachusetts, and is within 32 kilometres of attractions including Plimoth Patuxet Museums, the New Bedford Whaling Museum, Sandwich Glass Museum, and Heritage Museums & Gardens.
This 167 square metre property sleeps up to 19 guests in one bedroom and one bathroom, boasting a fully equipped kitchen, terrace with sea views, private beach access, free Wi-Fi, parking, and a fireplace.
Hawley Home W/ Deck: 4 Mi To Berkshire East Resort - Massachusetts
10 3 reviews

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

house, Hawley
This self-catering house near Hawley, Pennsylvania, is 45km from The Clark Art Institute and 103km from Albany International Airport.
The 69 square metre property offers one bedroom, one bathroom, sleeping up to five guests, and features a fully equipped kitchen, Wi-Fi, a washing machine, and a tennis court.
2 Twin Beds On 1st Floor With En-suite Bathroom. - Massachusetts
No reviews

2 Twin Beds On 1st Floor With En-suite Bathroom.

apartment, Shelburne
This pet-friendly flat in Shelburne Falls is a short walk from Glacial Potholes, Shelburne Falls, and the Bridge of Flowers, and is also near G. William Pitt House and Collection, Catamount State Forest, and Shelburne Falls Bowling Alley.
This one-bedroom flat accommodates two guests and features a full kitchen, air conditioning, on-site parking, and offers on-site kayaking.
Nantucket Style Cottage Steps From Private Beach - Massachusetts
10 49 reviews

Nantucket Style Cottage Steps From Private Beach

cottage, Mashpee
This charming cottage is situated in Popponesset, a short walk from the Popponesset Marketplace and a short drive from Mashpee Commons, offering a peaceful retreat with easy access to local amenities. Guests have consistently rated the cottage excellent for its location, cleanliness, and overall experience.
The two-bedroom cottage comfortably sleeps six guests, providing a spacious and comfortable living space. Enjoy modern amenities, a private beach just steps away, a scenic backyard with balconies, and a BBQ for al fresco dining.
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