Best Vacation Homes in Massachusetts
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $307/Night
For 7 Nights US $2,150
449.39 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Bed & Breakfast
- Pool
- Balcony/Terrace
- Parking
US $408/Night
For 7 Nights US $2,856
1 ft²
12 Guests
6 Bedrooms
6 Bathrooms
Group Friendly
House
US $2,086/Night
For 7 Nights US $14,602
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
US $335/Night
For 7 Nights US $2,346
645.83 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
US $249/Night
For 7 Nights US $1,743
1600 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $477/Night
For 7 Nights US $3,336
1100 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $307/Night
For 7 Nights US $2,150
1350 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Ski Chalet
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $259/Night
For 7 Nights US $1,810
Massachusetts Luxury Rentals
3702.79 ft²
8 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
House
- Pet Friendly
- Parking
- Air Conditioner
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2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Breakfast
- Kitchen
- Air Conditioner
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4 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
House
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5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
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8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
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14 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Breakfast
- Kitchen
- Air Conditioner
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468 ft²
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Hotel
- Fireplace/Heating
- Air Conditioner
- Internet
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Massachusetts Pet Friendly Vacation Rentals
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Skiing
- Fireplace/Heating
- Ocean View
US $307/Night
For 7 Nights US $2,150
1097.92 ft²
5 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $268/Night
For 7 Nights US $1,874
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $631/Night
For 7 Nights US $4,415
1500 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,577
1248.61 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $332/Night
For 7 Nights US $2,322
800 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $322/Night
For 7 Nights US $2,251
1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $357/Night
For 7 Nights US $2,501
450 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Private Pool
- Fireplace/Heating
- Pool
US $293/Night
For 7 Nights US $2,052
Massachusetts Large Vacation Homes
10 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $242/Night
For 7 Nights US $1,696
291.53 ft²
26 Guests
13 Bedrooms
13 Bathrooms
Bed & Breakfast
- Parking
- Air Conditioner
- Internet
US $168/Night
For 7 Nights US $1,176
16 Guests
6 Bedrooms
6 Bathrooms
Group Friendly
House
US $1,105/Night
For 7 Nights US $7,733
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
US $271/Night
For 7 Nights US $1,899
12.55 ft²
15 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $170/Night
For 7 Nights US $1,190
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
US $244/Night
For 7 Nights US $1,705
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $577/Night
For 7 Nights US $4,038
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
US $210/Night
For 7 Nights US $1,470
Why Choose Rent By Owner for your Massachusetts Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Massachusetts
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as seasonal variations in Massachusetts offer a range of activities and scenery that suit different preferences throughout the year.
Peak Season Highlights
Summer (June to August)
During the warmest months, you'll enjoy plentiful outdoor activities and vibrant local events in the area, making it an ideal time for a lively vacation experience.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to November)
In this scenic season, expect breathtaking foliage and cooler temperatures that create a perfect setting for exploring the region's natural beauty and cultural attractions.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
While the winter months see fewer visitors, you can still enjoy a peaceful retreat with opportunities for cozy indoor activities and winter scenery in the region.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
Spring (March to May)
Early spring offers a quieter atmosphere with blossoming landscapes and milder weather, ideal for those seeking a more relaxed visit before the summer rush begins.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Massachusetts
How to Book Your Massachusetts Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Massachusetts
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool for relaxing days in the sun.
- Take advantage of spacious patios or decks perfect for outdoor dining and gatherings.
- Benefit from lush landscaped gardens or yard space ideal for outdoor activities.
- Make use of outdoor grills or barbecues to cook up local flavors.
- Explore nearby walking trails or biking paths accessible directly from your rental.
- Relax on comfortable outdoor furniture while soaking in scenic views of the region.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
Top Attractions Around Massachusetts
What attractions are nearby?
In this region, you can explore a variety of outdoor activities, cultural experiences, and scenic attractions that showcase the best of Massachusetts' rich history and natural beauty, all easily accessible from your chosen vacation rentals.
Family Activities
- Boston Children's Museum: Engage your family with interactive exhibits and hands-on learning experiences in the vibrant city of Boston, where educational fun is guaranteed for kids of all ages.
- Plimoth Plantation: Step back in time at this historical site that offers immersive history lessons about early American life, perfect for families exploring the region’s rich heritage.
- New England Aquarium: Discover marine life through captivating exhibits and an impressive IMAX theater, making it a must-visit destination for families interested in oceanography here.
- Canobie Lake Park: Enjoy a day filled with rides, attractions, and entertainment at this popular amusement park, ideal for family outings during your stay in Massachusetts.
Adult Activities
- Exploring the Freedom Trail: Walk along this historic pathway to discover centuries of American history through notable sites and landmarks in the city.
- Visiting Martha’s Vineyard: Enjoy the scenic beauty and charming villages of this island, perfect for a relaxing day trip or an extended stay in cozy vacation rentals.
- Participating in Boston's Food Tours: Taste your way through local culinary favorites on guided tours that showcase the region’s diverse and vibrant food scene.
- Discovering Mystic Seaport Museum: Dive into maritime history at this renowned museum, where you can explore historic ships and engaging exhibits right here in New England.
Other Places to Stay in Massachusetts, MA
Barnstable County
Cape Cod
Boston
Suffolk County
Middlesex County
North Shore
Essex County
Dukes County
Martha's Vineyard
Berkshire County
The Berkshires
Nantucket
Massachusetts Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Highlights: Take advantage of the region’s unique attractions by planning your itinerary around the area's renowned cultural and natural sites.
- Book Early for Popular Seasons: Secure your preferred vacation rentals well in advance to enjoy prime locations and avoid last-minute availability issues.
- Embrace Regional Cuisine: Savor the flavors of local delicacies at nearby eateries or prepare meals using fresh ingredients from local markets in your rental.
- Navigate Transportation Options: Familiarize yourself with the region’s public transit and driving routes to maximize convenience during your stay.
Transportation Options
- Massachusetts Bay Transportation Authority (MBTA): You can rely on the MBTA for extensive subway, bus, and commuter rail services that connect major cities and towns across the area.
- Rental Cars: Renting a car provides flexibility and convenience to explore both urban attractions and scenic coastal areas at your own pace.
- Amtrak trains: Amtrak offers comfortable train connections between here and other Northeast destinations, ideal for travelers seeking a scenic and relaxing journey.
- Ferries: With picturesque ferry routes available, you can enjoy a scenic waterway transit to nearby islands and coastal communities, enhancing your regional experience.
Local Customs Options
- Respect for Local Historic Traditions: You’ll find that honoring the area's rich historical heritage is a key part of experiencing here in Massachusetts, especially by participating in community events and respecting preserved sites.
- Attire During Cultural Celebrations: When visiting during local festivals or traditions, dressing in a manner that respects the regional customs can enrich your experience and show appreciation for the community’s heritage.
- Greeting Etiquette: A warm, friendly greeting is common when engaging with locals, reflecting the welcoming spirit that characterizes this region's social interactions.
- Dining Customs: Embracing regional food traditions, such as seafood-based dishes, not only enhances your culinary experience but also demonstrates respect for local dining customs.
Frequently Asked Questions About Massachusetts?
1. What are the top vacation rentals in Massachusetts?
There are a lot of options in Massachusetts. If you plan on staying in the Massachusetts area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Massachusetts:
- Boston Yacht Haven Inn & Marina
- Near Boston Historic two-bedroom with Modern Amenities
- Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
- Leslie's Retreat: Spacious home ideally located to everything
- The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
- Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
- Steps to the Ocean! Perfect Location!
- Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
- Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!
- Two bedroom condo near to everything Ptown has to offer
2. How many vacation rentals have private pools in Massachusetts?
There are 1477 vacation rentals with private pools near Massachusetts. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Massachusetts are best for families?
If you are looking for a family-friendly vacation home in Massachusetts, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Massachusetts:
4. How many Rentbyowner vacation rentals are available in Massachusetts?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 30766 in the Massachusetts area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Massachusetts.
5. What is the cancellation policy for vacation rentals here?
Cancellation policies vary depending on the property listing. You should review the specific policy detailed in the rental listing or contact the owner directly to understand any fees or restrictions involved.
6. Are there any additional fees I should be aware of when booking a vacation rental?
Additional fees such as cleaning fees, service charges, or local taxes are often included in the listing details. It’s best to read the full description or reach out to the owner to clarify any extra costs before confirming your reservation.
7. How do I ensure my stay complies with the local regulations and rules?
All property listings include guidelines and house rules set by the owner. Make sure to review these rules carefully before booking, and contact the owner if you have any questions about compliance during your stay.
8. Can I modify or extend my reservation after booking?
Modification or extension requests depend on the owner’s policies and availability. Check the listing details for flexibility options or contact the owner directly to discuss any changes to your reservation.
9. What amenities are typically available in vacation rentals in this area?
The amenities offered can vary, but common features include Wi-Fi, fully equipped kitchens, and parking. For specific amenities, review the property listing thoroughly or contact the owner to confirm what is included.
Massachusetts Top Rated Vacation Rentals
920 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Spa
- Fireplace/Heating
US $660/Night
For 7 Nights US $4,618
620 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
US $263/Night
For 7 Nights US $1,839
1280 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Spa
- Fireplace/Heating
US $1,358/Night
For 7 Nights US $9,504
1725 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Spa
- Fireplace/Heating
US $2,294/Night
For 7 Nights US $16,056
1 Bedroom
1 Bathroom
Ocean View
Bed & Breakfast
- Pool
- Ocean View
- Balcony/Terrace
US $235/Night
For 7 Nights US $1,642
2501 ft²
6 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $461/Night
For 7 Nights US $3,228
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Fireplace/Heating
- Pool
US $144/Night
For 7 Nights US $1,006
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Oceanfront
- Spa
- Fireplace/Heating
US $641/Night
For 7 Nights US $4,486
