The 30 Best Holiday Rentals in Boston Metropolitan Area

Ranked 1 out of 275 in the 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 2 out of 275 in the 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 3 out of 275 in the 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 4 out of 275 in the 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 5 out of 275 in the 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 6 out of 275 in the 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 7 out of 275 in the 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 8 out of 275 in the 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 9 out of 275 in the 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 10 out of 275 in the 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 11 out of 275 in the region, as well as being 8 of 138 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!

Ranked 12 out of 275 in the region, as well as being 9 of 138 for holiday rentals in Boston.

• “The room could not have been more perfect for our three-night visit to Beacon Hill.”
• “Wish I had known before about this place.”
• “Great location,very clean apartment with lovely bathroom and...”
• See more reviews of 94 Charles Street by Thatch

Ranked 13 out of 275 in the region, as well as being 10 of 138 for holiday rentals in Boston.

• “Great Place”
• “Lovely accommodation, not far from the city centre”
• “Stay wag good. Attractions were fun but expensive”
• See more reviews of Boston Queen Bedroom

Ranked 14 out of 275 in the region, as well as being 11 of 138 for holiday rentals in Boston.

• “Just what we needed”
• “Great attention to detail --coffee, toothbrushes, slippers,...”
• “Like at home!”
• See more reviews of Unique & Peaceful Boston Home( Free Parking)

Ranked 15 out of 275 in the region, as well as being 12 of 138 for holiday rentals in Boston.

• “Perfect”
• “Great location and very comfortable and clean.”
• “Would stay here again if traveling solo”
• See more reviews of Stylish Studio on Newbury St #3

Ranked 16 out of 275 in the region, as well as being 13 of 138 for holiday rentals in Boston.

• “Excellent location and very clean. I'd stay here again.”
• “It was practical and efficient; If we have a large party looking to stay all together we will likely try it again.”
• “Perfect location. Very comfortable rooms.”
• See more reviews of Sonder at Pierce Boston

Ranked 17 out of 275 in the region, as well as being 14 of 138 for holiday rentals in Boston.

• “Spacious house, great host”
• “Good value, lots of space.”
• “Was comfortable with great location , but it’s a very old house needs a lot of renovations. It also had some bugs .”
• See more reviews of Boston Historical Urban Oasis

Ranked 18 out of 275 in the region, as well as being 15 of 138 for holiday rentals in Boston.

• “It was a great stay!”
• “Served the purpose”
• “I liked the location and the close proximity to shopping...”
• See more reviews of Beautiful Townhouse, 2 bedrooms, 2 bath

Ranked 19 out of 275 in the region, as well as being 1 of 4 for holiday rentals in Stoneham.

• “No issues with keys, finding the parking spot.”
• “It was perfect for the amount of time that we were visiting family for the holidays.”
• “Beautiful wide open condo.”
• See more reviews of Modern Two Bedroom Condo - Boston

Ranked 20 out of 275 in the region, as well as being 16 of 138 for holiday rentals in Boston.

• “Good location, although quite noisy.”
• “Loved my stay in 234 Newbury Street. Would definitely recommend.”
• “Great stay!”
• See more reviews of Sonder The Magnolia

Ranked 21 out of 275 in the region, as well as being 17 of 138 for holiday rentals in Boston.

• “Our stay was incredibly peaceful and comfortable, thanks to the spotless environment and the warm hospitality of the own”
• “A wonderful 1 bedroom flat with off-street parking and wifi located near public transit and highway.”
• “It was a relaxing 3 weeks”
• See more reviews of Boston Luxury 2 Bedroom Private Condo

Ranked 22 out of 275 in the region, as well as being 18 of 138 for holiday rentals in Boston.

• “A great option for a family getaway in Boston”
• “Very convenient for facilities & public transport into Boston”
• “Great location, great facilities and contact. Just be aware of steep stairs.”
• See more reviews of Location+Comfort+Convenience

Ranked 23 out of 275 in the region, as well as being 4 of 9 for holiday rentals in Quincy.

• “A side from the beds, the experience was great.”
• “Pretty convenient, near Boston.”
• “Excellent location very clean property”
• See more reviews of Park view South of Boston - Quincy

Ranked 24 out of 275 in the region, as well as being 19 of 138 for holiday rentals in Boston.

• “Great location, great service”
• “Excellent location!”
• “Location!”
• See more reviews of Furnished Newbury Street Studio, #6

Ranked 25 out of 275 in the region, as well as being 20 of 138 for holiday rentals in Boston.

• “EXPENSIVE and DISAPPOINTING”
• “We had a great time on Boston.”
• “Amazing location, have your own strong WiFi.”
• See more reviews of Stylish Newbury Street Studio, #4

Ranked 26 out of 275 in the region, as well as being 21 of 138 for holiday rentals in Boston.

• “Good value for money;”
• “Good pleasant location (walking area, close to the Common...”
• “Basic accommodations in a good neighborhood.”
• See more reviews of Charming & Stylish Studio on Beacon Hill #15

Ranked 27 out of 275 in the region, as well as being 22 of 138 for holiday rentals in Boston.

• “This is a lovely apartment, centrally located and really nicely fitted out and thoughtfully equipped. Lots of steep stai”
• “Perfect location. Would have been a 10/10 if the water had stayed warm enough for long showers and hot baths.”
• “Truly, a sense of living in Boston, not merely being a tourist.”
• See more reviews of 304 Newbury Street by Thatch

Ranked 28 out of 275 in the region, as well as being 23 of 138 for holiday rentals in Boston.

• “You get what you pay for in Boston. Sometimes worse.”
• “Spacious apartment with great views.”
• “Clean, sweet host, horrible location!”
• See more reviews of 90-Boston Spacious Convenient Apartment

Ranked 29 out of 275 in the region, as well as being 24 of 138 for holiday rentals in Boston.

• “Very Comfortable Home”
• “Perfect for me!”
• “Very grateful to Suzana who greeted us and a beautifully appointed home away from home.”
• See more reviews of Cozy Boston Getaway Apartment

Ranked 30 out of 275 in the region, as well as being 2 of 2 for holiday rentals in Everett.

• “It felt home from home.”
• “Had a great”
• “Very clean, well stocked with towels and the soap in the...”
• See more reviews of Cozy Getaway