The 30 Best Holiday Rentals in Massachusetts

Ranked 1 out of 967 in the Massachusetts region, as well as being 1 of 19 for holiday rentals in Falmouth.

• “Wonderful!”
• “Exceptional apartment”
• “Peaceful beach side retreat.”
• See more reviews of InnSeason Resorts Captain's Quarters

Ranked 2 out of 967 in the Massachusetts region, as well as being 4 of 19 for holiday rentals in Falmouth.

• “A beautiful retreat close to home”
• “Overall good after some early hiccups.”
• “Great Place to Stay!”
• See more reviews of InnSeason Resorts Surfside

Ranked 3 out of 967 in the Massachusetts region, as well as being 3 of 16 for holiday rentals in Gloucester.

• “Great stay, no issues, easy to reach host. Would recommend”
• “Cozy Home Away from Home”
• “Loved it here, would definitely recommend.”
• See more reviews of Retreat near Beaches

Ranked 4 out of 967 in the Massachusetts region, as well as being 1 of 131 for holiday rentals in Boston.

• “Great but Noise from above Apt stopped it from being Awesome.”
• “I would stay here again upon checking if the items we pointed out were addressed.”
• “It was lovely to spend some time in the suburbs after holidaying on major cities. The property was amazing for us”
• See more reviews of Roslindale village condos

Ranked 5 out of 967 in the Massachusetts region, as well as being 1 of 7 for holiday rentals in North Truro.

• “Beautiful and comfortable spot on the beach.”
• “I would stay there again.”
• “Excellent!”
• See more reviews of Sandbars Inn

Ranked 6 out of 967 in the Massachusetts region, as well as being 1 of 1 for holiday rentals in Northfield.

• “Cute place if they fixed these major issues it would be a nice place to stay.”
• “Great place, great location!”
• “I would return even if I had no reason to be in that area!!”
• See more reviews of Rustic-Chic Cottage with Yard and Grill - Near Hiking!

Ranked 7 out of 967 in the Massachusetts region, as well as being 1 of 2 for holiday rentals in Everett.

• “grth”
• “Amazing & Wonderful!! Get a Charlie card for public transport.”
• “Excellent, clean and convenient location with a great host. Highly recommend.”
• See more reviews of Cozy condo with all perks & parking close to Encore Casino

Ranked 8 out of 967 in the Massachusetts region, as well as being 1 of 5 for holiday rentals in Cambridge.

• “Nice staying”
• “Everything.”
• “Host was so nice.”
• See more reviews of Comfortable Whole Apartment 1 Bed 1 Bath at Harvard-MIT

Ranked 9 out of 967 in the Massachusetts region, as well as being 2 of 131 for holiday rentals in Boston.

• “Place was really good”
• “From here and Beyond”
• “A kid friendly apartment good for small families.”
• See more reviews of ~*30min to Downtown*~ THE COSMOPOLITAN

Ranked 10 out of 967 in the Massachusetts region, as well as being 1 of 1 for holiday rentals in Lynn.

• “Amazing stay! Juan really helped out when we forgot something in the place. A beautiful place”
• “Great place to stay”
• “This location was as described and Juan was very nice and accommodating”
• See more reviews of Farmhouse 2 bedrooms apartment

Ranked 11 out of 967 in the Massachusetts region, as well as being 3 of 131 for holiday rentals in Boston.

• “A lovely five night stay in Boston”
• “Very comfortable and great value stay. Just removed enough from the city but still convenient!”
• “Great space for coworkers traveling together!”
• See more reviews of Near Train Station Gorgeous 3-Bedroom Apartment with Patios

Ranked 12 out of 967 in the Massachusetts region, as well as being 4 of 131 for holiday rentals in Boston.

• “Parking spot included, nice amenities (laundry, kitchen, bath), and plenty of room.”
• “Outside Boston”
• “Beautiful and enchanting”
• See more reviews of Bright & Spacious 2Br apartment, mins from Downtown Boston, parking

Ranked 13 out of 967 in the Massachusetts region, as well as being 2 of 16 for holiday rentals in Plymouth.

• “Everything was fine.”
• “Lovely apartment.”
• “Excellent. Would stay again in a heartbeat!”
• See more reviews of Harbourtown Suites on Plymouth Harbor

Ranked 14 out of 967 in the Massachusetts region, as well as being 7 of 16 for holiday rentals in Gloucester.

• “Small details to suggest for the host: ”
• “Right in the heart of Gloucester and we were able to walk to...”
• “very friendly hosts and very nicely furnished comfortable apartment”
• See more reviews of Guest suite in historical district

Ranked 15 out of 967 in the Massachusetts region, as well as being 10 of 26 for holiday rentals in Nantucket.

• “House was beautiful.”
• “We had a wonderful long weekend with friends. Thank you for sharing your home.”
• “Fantastic stay in Nantucket! House was very comfortable and close to eastern coast beaches”
• See more reviews of 9 Green Hollow Road

Ranked 16 out of 967 in the Massachusetts region, as well as being 8 of 16 for holiday rentals in Gloucester.

• “I felt taken advantage of.”
• “Great location and amenities!”
• “Relaxing weekend for my husband and I.”
• See more reviews of CbytheSea - Ocean View Penthouse

Ranked 17 out of 967 in the Massachusetts region, as well as being 5 of 131 for holiday rentals in Boston.

• “A wonderful value for money stay in Boston!”
• “Great place!”
• “It’s my best decision to choose this appartement when I planned the Boston trip!”
• See more reviews of The Boston Rental - Multiple Floorplans

Ranked 18 out of 967 in the Massachusetts region, as well as being 1 of 5 for holiday rentals in Provincetown.

• “It was very clean.”
• “One of the cleanest and most comfortable places I have ever stayed in!”
• “My apartment was SPOTLESS!”
• See more reviews of Eastwood at Provincetown

Ranked 19 out of 967 in the Massachusetts region, as well as being 1 of 5 for holiday rentals in Mashpee.

• “Everything was perfect”
• “Clean, quiet neighborhood. Great condo!”
• “Disappointing”
• See more reviews of The Club at New Seabury

Ranked 20 out of 967 in the Massachusetts region, as well as being 2 of 4 for holiday rentals in Newton.

• “A luxurious home from home.”
• “The location and property was amazing. It was a beautiful place to stay and very homey. My family and I loved it. We wou”
• “Stas - you rock! Thank you for a very comfortable stay!”
• See more reviews of The Inn at Newton Highlands

Ranked 21 out of 967 in the Massachusetts region, as well as being 2 of 5 for holiday rentals in Marblehead.

• “We enjoyed every minute of our stay and cannot wait to go back!”
• “The property was perfect for our weekend stay.”
• “Best part of the Trip!”
• See more reviews of An authentic, rustic luxurious little single family home in Old Town. All yours.

Ranked 22 out of 967 in the Massachusetts region, as well as being 2 of 8 for holiday rentals in Framingham.

• “Great place to stay while visiting Framingham-Go FSU Rams!”
• “Great, clean comfortable stay close enough to route 9 and the turnpike so very convenient. Not too far from Boston witho”
• “Bright and modern apartment”
• See more reviews of Private Luxury Framingham condo near Boston

Ranked 23 out of 967 in the Massachusetts region, as well as being 8 of 17 for holiday rentals in Edgartown.

• “Never again”
• “great visit in and out”
• “Nice place, good location.”
• See more reviews of Edgartown Commons Vacation Apartments

Ranked 24 out of 967 in the Massachusetts region, as well as being 1 of 1 for holiday rentals in Handy Four Corners.

• “It was ok- for the cost I could have gotten a nicer hotel room.”
• “Nice cabin nearby ocean bay.”
• “Great location, need more cleaning and amenities”
• See more reviews of 1 bed cottage, water views & water access

Ranked 25 out of 967 in the Massachusetts region, as well as being 4 of 16 for holiday rentals in Plymouth.

• “It was a very nice stay!”
• “Our family had a wonderful first visit and plan to return soon.”
• “Great house and owner was great at communicating!”
• See more reviews of presidents

Ranked 26 out of 967 in the Massachusetts region, as well as being 11 of 16 for holiday rentals in Gloucester.

• “Excellent”
• “Great space.”
• “Great well stocked property for a two night stay”
• See more reviews of Ocean Breeze-8min Walk to Beach

Ranked 27 out of 967 in the Massachusetts region, as well as being 1 of 5 for holiday rentals in Truro.

• “great place to get away from it all”
• “We enjoyed our stay it was a short ride to p town”
• “Time to relax and unwind”
• See more reviews of Truro Beach Cottages

Ranked 28 out of 967 in the Massachusetts region, as well as being 6 of 131 for holiday rentals in Boston.

• “Property was very clean and the beds and couches were very...”
• “Recommend accommodations for other travelers.”
• “Excellent property exceeded our expectations”
• See more reviews of ~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Ranked 29 out of 967 in the Massachusetts region, as well as being 3 of 4 for holiday rentals in Watertown.

• “Great location and space.”
• “The stay was great. Alex was very helpful. The description and photos are true. Great location.”
• “This apartment is a Winner!”
• See more reviews of Luxury 3 bdr apt with backyard and off-street parking

Ranked 30 out of 967 in the Massachusetts region, as well as being 7 of 131 for holiday rentals in Boston.

• “I wish to come here again”
• “A great location with host we’re we’re available whenever you need them!”
• “Fantastic! Marvelous!”
• See more reviews of Beautiful Apartment-5 Beds-Full Kitchen-Parking-Super Clean!