Vacation Rentals inMassachusetts
Massachusetts has 10 vacation rentals, with the most in Barre, Chatham, and Edgartown. They sleep 12 to 35 guests overnight. Common features include amazing views, fishing, and game room. 10 have guest reviews, averaging 4.9 out of 5.
Best Vacation Rentalsin Massachusetts
Showing 10 of 10 venues
Stunning Modern Masterpiece on the Beach in Truro RPAM031
4.9Stunning Modern Masterpiece on the Beach in Truro RPAM031 Welcome to 21 Crestview Circle in Truro, MA: an iconic, modernist sanctuary where architecture, art, and nature coalesce to create an unparalleled experience on the shore of Cape Cod Bay. This avant-garde estate is a bold…
The Kemble- Built by a US Secretary of State in Lenox
4.9The Kemble Berkshires is a registered Great Estatebuilt in the 1880s for a U.S. Secretary of State and New Jersey State Senator - nownewly renovated byShared Estates with bright minimalist finishes and world-class amenities. The property has manicured landscaping with massive rol…
Luxurious Captain's Mansion - Waterfront, Town, & Beaches - 5 stars
4.9Captain Morse House Luxury - In Town, Walk to Waterfront, Beach, Pets, 5 stars The Captain Morse House is located on the iconic North Water Street in Edgartown on Martha's Vineyard. It was built by the island's most successful whaling Captain in 1840. The Captain Morse House has…
Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!
5.0Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym! This Magnificent 7000 SF, Air Conditioned, 10 year old Estate is in pristine condition. It is located on 4 acres of privacy and abuts 8 acres of open space. You can relax and enjoy your morning coffee…
Stage Island Estate - New Availability Waterfront with Pool and Private Dock
4.5Stage Island Estate - New Availability Waterfront with Pool and Private Dock This home is represented by Nauset Rental, a local vacation rental management company. Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting…
Luxury home with 2 pools, (indoor and outdoor)dock, hot tub and more! RPMS081
4.9Luxury home with 2 pools on the water. RPMS081 Michelle Sylvia high-end collection rental home. NEW for 2025, indoor hot tub. Overlooking the sparkling waters of Prince Cove this Contemporary waterfront property with Deep Water Dock provides easy access to Nantucket Sound. This l…
Unobstructed Direct Oceanfront in Seaside Boston/Nahant
5.0Spacious, oceanfront home at water's edge. Unspoiled panoramic views of the ocean and coastline from an expanse of windows. Mesmerizing views of the ocean from every room. Five/six bedrooms plus additional sleeping on futons & and roll-away beds. Relaxing on the 45 ft deck wi…
"Second Wind" - An Orleans Estate with large heated pool, on Town Cove: 039-O; sleeps 24
5.0"Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 This property is professionally managed by Pretty Picky Properties. "Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove Sleeps up to 24 in three dwellings Linens an…
Your Own Personal Tiki-Hut Paradise On John's Pond RPAM033
4.9Your Own Personal Tiki-Hut Paradise On John's Pond RPAM033 A waterfront paradise awaits you and your guests at THE premier John's Pond vacation rental. Featuring a private white sand beach with a large dock, Tiki Hut with cable TV and plenty of waterfront seating this home offers…
Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
4.9Located in the historic town of Barre, just off the Commons is this unassuming, yet sprawling property. This house features five bedrooms, six bathrooms, seven fireplaces, a large lodge-like family room that doubles as a game room, equipped with pool, foosball, and air-hockey tab…
Stunning Modern Masterpiece on the Beach in Truro RPAM031
4.9Massachusetts
Stunning Modern Masterpiece on the Beach in Truro RPAM031 Welcome to 21 Crestview Circle in Truro, MA: an iconic, modernist sanctuary where architecture, art, and nature coalesce to create an unparalleled experience on the shore of Cape Cod Bay. This avant-garde estate is a bold…
The Kemble- Built by a US Secretary of State in Lenox
4.9Massachusetts
The Kemble Berkshires is a registered Great Estatebuilt in the 1880s for a U.S. Secretary of State and New Jersey State Senator - nownewly renovated byShared Estates with bright minimalist finishes and world-class amenities. The property has manicured landscaping with massive rol…
Luxurious Captain's Mansion - Waterfront, Town, & Beaches - 5 stars
4.9Massachusetts
Captain Morse House Luxury - In Town, Walk to Waterfront, Beach, Pets, 5 stars The Captain Morse House is located on the iconic North Water Street in Edgartown on Martha's Vineyard. It was built by the island's most successful whaling Captain in 1840. The Captain Morse House has…
Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!
5.0Massachusetts
Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym! This Magnificent 7000 SF, Air Conditioned, 10 year old Estate is in pristine condition. It is located on 4 acres of privacy and abuts 8 acres of open space. You can relax and enjoy your morning coffee…
Stage Island Estate - New Availability Waterfront with Pool and Private Dock
4.5Massachusetts
Stage Island Estate - New Availability Waterfront with Pool and Private Dock This home is represented by Nauset Rental, a local vacation rental management company. Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting…
Luxury home with 2 pools, (indoor and outdoor)dock, hot tub and more! RPMS081
4.9Massachusetts
Luxury home with 2 pools on the water. RPMS081 Michelle Sylvia high-end collection rental home. NEW for 2025, indoor hot tub. Overlooking the sparkling waters of Prince Cove this Contemporary waterfront property with Deep Water Dock provides easy access to Nantucket Sound. This l…
Unobstructed Direct Oceanfront in Seaside Boston/Nahant
5.0Massachusetts
Spacious, oceanfront home at water's edge. Unspoiled panoramic views of the ocean and coastline from an expanse of windows. Mesmerizing views of the ocean from every room. Five/six bedrooms plus additional sleeping on futons & and roll-away beds. Relaxing on the 45 ft deck wi…
"Second Wind" - An Orleans Estate with large heated pool, on Town Cove: 039-O; sleeps 24
5.0Massachusetts
"Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 This property is professionally managed by Pretty Picky Properties. "Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove Sleeps up to 24 in three dwellings Linens an…
Your Own Personal Tiki-Hut Paradise On John's Pond RPAM033
4.9Massachusetts
Your Own Personal Tiki-Hut Paradise On John's Pond RPAM033 A waterfront paradise awaits you and your guests at THE premier John's Pond vacation rental. Featuring a private white sand beach with a large dock, Tiki Hut with cable TV and plenty of waterfront seating this home offers…
Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!
4.9Massachusetts
Located in the historic town of Barre, just off the Commons is this unassuming, yet sprawling property. This house features five bedrooms, six bathrooms, seven fireplaces, a large lodge-like family room that doubles as a game room, equipped with pool, foosball, and air-hockey tab…
Frequently Asked Questions
How many vacation rentals are in Massachusetts?
There are 10 vacation rentals listed in Massachusetts, spread across 10 cities and towns.
Which cities in Massachusetts have the most vacation rentals?
Barre, Chatham, and Edgartown have the most, with 1 each.
How many people do Massachusetts vacation rentals sleep?
10 rentals list their sleeping capacity, from 12 to 35 people.
How are Massachusetts vacation rentals rated?
10 of 10 listings have guest reviews, with an average rating of 4.9 out of 5.
What amenities are most common at Massachusetts vacation rentals?
Amazing Views is the most common (10 listings), followed by fishing (8) and game room (7).
What's the most popular vacation rental style in Massachusetts?
Estate properties are the most common in Massachusetts, with 4 to choose from, alongside other styles. Filter by property style to match what you want.
Are there vacation rentals with outdoor space in Massachusetts?
Yes, 5 of Massachusetts's vacation rentals offer outdoor space, from gardens and pools to waterfront settings.
Are there beachfront vacation rentals in Massachusetts?
Yes, Massachusetts has 2 beachfront or oceanfront vacation rentals for a waterside stay.