The 30 Best Holiday Rentals in Massachusetts

Ranked 1 out of 1,035 in the Massachusetts region, as well as being 1 of 20 for holiday rentals in Falmouth.

• “Wonderful respite”
• “Wonderful!”
• “Exceptional apartment”
• See more reviews of InnSeason Resorts Captain's Quarters

Ranked 2 out of 1,035 in the Massachusetts region, as well as being 2 of 18 for holiday rentals in Gloucester.

• “Nice placed but ruined by intrusive owner.”
• “Pleasant”
• “Great place. Great host”
• See more reviews of Retreat near Beaches

Ranked 3 out of 1,035 in the Massachusetts region, as well as being 4 of 20 for holiday rentals in Falmouth.

• “Nice view and comfy rooms”
• “Very relaxing! We will definitely stay here again”
• “A beautiful retreat close to home”
• See more reviews of InnSeason Resorts Surfside

Ranked 4 out of 1,035 in the Massachusetts region, as well as being 1 of 17 for holiday rentals in Plymouth.

• “Comfortable, accessible to the waterfront.”
• “One night stay, place would be great for a long weekend. Plymouth is a great walking town, this prime location is perfec”
• “New spacious condo”
• See more reviews of Thomas Sea Suites at Harbourtown

Ranked 5 out of 1,035 in the Massachusetts region, as well as being 1 of 138 for holiday rentals in Boston.

• “Utter perfection for our family of four’s five nt stay!! We will be back for certain!!”
• “Great place, wish I could say the same about the owners/operators”
• “Excellent”
• See more reviews of Roslindale village condos

Ranked 6 out of 1,035 in the Massachusetts region, as well as being 1 of 8 for holiday rentals in North Truro.

• “It was a short getaway for my birthday and it was perfect”
• “Perfect for multi-unit on beach property”
• “Super clean, the kitchenette was equipped.”
• See more reviews of Sandbars Inn

Ranked 7 out of 1,035 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 1,035 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 9 out of 1,035 in the Massachusetts region, as well as being 1 of 2 for holiday rentals in Lynn.

• “Nice decoration in a very cute old apartment”
• “It's good for money”
• “Everything you need in Lynn”
• See more reviews of Farmhouse 2 bedrooms apartment

Ranked 10 out of 1,035 in the Massachusetts region, as well as being 2 of 138 for holiday rentals in Boston.

• “Overall ok, but hoped for better at this price.”
• “I would be stay again.”
• “Place was really good”
• See more reviews of ~*30min to Downtown*~ THE COSMOPOLITAN

Ranked 11 out of 1,035 in the Massachusetts region, as well as being 3 of 138 for holiday rentals in Boston.

• “Excellent stay for our Boston experience”
• “Very nice stay - everything as per ad/booking info and very service minded landlord/manager.”
• “Parking spot included, nice amenities (laundry, kitchen, bath), and plenty of room.”
• See more reviews of Bright & Spacious 2Br apartment, mins from Downtown Boston, parking

Ranked 12 out of 1,035 in the Massachusetts region, as well as being 4 of 138 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 13 out of 1,035 in the Massachusetts region, as well as being 3 of 17 for holiday rentals in Plymouth.

• “Great View Great Room !”
• “We were there for a family wedding. This was a convenient place to stay.”
• “First class location & facilities.”
• See more reviews of Harbourtown Suites on Plymouth Harbor

Ranked 14 out of 1,035 in the Massachusetts region, as well as being 7 of 18 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 1,035 in the Massachusetts region, as well as being 9 of 28 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 1,035 in the Massachusetts region, as well as being 8 of 18 for holiday rentals in Gloucester.

• “Location was ideal and the views of the Gloucester Harbor...”
• “I felt taken advantage of.”
• “Great location and amenities!”
• See more reviews of CbytheSea - Ocean View Penthouse

Ranked 17 out of 1,035 in the Massachusetts region, as well as being 5 of 138 for holiday rentals in Boston.

• “We like that the rooms are very comfortable and the...”
• “A wonderful value for money stay in Boston!”
• “Great place!”
• See more reviews of The Boston Rental - Multiple Floorplans

Ranked 18 out of 1,035 in the Massachusetts region, as well as being 2 of 9 for holiday rentals in Framingham.

• “Would definitely stay here again!”
• “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”
• See more reviews of Private Luxury Framingham condo near Boston

Ranked 19 out of 1,035 in the Massachusetts region, as well as being 1 of 6 for holiday rentals in Provincetown.

• “Very peaceful. Will go agian”
• “It wasn’t crowded and was quite almost the whole time we...”
• “Fine for one night.”
• See more reviews of Eastwood at Provincetown

Ranked 20 out of 1,035 in the Massachusetts region, as well as being 2 of 6 for holiday rentals in Marblehead.

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

Ranked 21 out of 1,035 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 22 out of 1,035 in the Massachusetts region, as well as being 4 of 17 for holiday rentals in Plymouth.

• “It was a great little house to throw a little girls night.”
• “It was a very nice stay!”
• “Our family had a wonderful first visit and plan to return soon.”
• See more reviews of presidents

Ranked 23 out of 1,035 in the Massachusetts region, as well as being 8 of 17 for holiday rentals in Edgartown.

• “Will be just fine IF air quality fixed”
• “Easy”
• “Great place, would probably stay again but not much space!”
• See more reviews of Edgartown Commons Vacation Apartments

Ranked 24 out of 1,035 in the Massachusetts region, as well as being 6 of 138 for holiday rentals in Boston.

• “The apartment was perfect, all staff provided, suggested”
• “Relaxing kid friendly space to enjoy everything Boston has to offer. We will stay here again when visiting!”
• “All perfect, and great communication”
• See more reviews of *Cozy, Convenient Boston. Indulge, you deserve it*

Ranked 25 out of 1,035 in the Massachusetts region, as well as being 1 of 1 for holiday rentals in Handy Four Corners.

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

Ranked 26 out of 1,035 in the Massachusetts region, as well as being 12 of 18 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 1,035 in the Massachusetts region, as well as being 7 of 138 for holiday rentals in Boston.

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

Ranked 28 out of 1,035 in the Massachusetts region, as well as being 1 of 6 for holiday rentals in Truro.

• “Best cottages that I've found”
• “The little house experience near the shore and P-town was a real vacation getaway in the off-season.”
• “We loved it! The location was perfect and the cabin was recently updated!”
• See more reviews of Truro Beach Cottages

Ranked 29 out of 1,035 in the Massachusetts region, as well as being 2 of 8 for holiday rentals in North Truro.

• “Great hotel.”
• “Stay here. The owners are amazing and it a pretty short bus into town. Which they’ll help with. I loved every minute of”
• “room right onto the beautiful beach / view of provincetown and coast”
• See more reviews of Horizons Beach Resort

Ranked 30 out of 1,035 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