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Compare 368 Vacation Homes in Chestnut Hill with updated reviews, rates, and availability.

Gorgeous Beacon Hills Studio next to State house

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay here. Room very clean and accommodations good. Nice area. Near State House and Park Street subway. "
The price is SAR 559
SAR 958 total
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Beacon Hills Studio next to State house

Charming 2-bedroom house in superb Boston with WiFi

8.0 out of 10, Very Good, (1)
"I had booked this same accommodation on another site who CANCELLED me. I immediately frantically contacted Beatrice who calmed me down assuring me I would have a reservation. She and I worked together and figured it out! I have already booked this accommodation for July 2025! There’s a great place to eat breakfast and any other time. Joe’s… about a 4 minute walk!!"
The price is SAR 650
SAR 1,101 total
includes taxes & fees
26 Nov - 27 Nov
Charming 2-bedroom house in superb Boston with WiFi

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

9.6 out of 10, Exceptional, (75)
"We loved this location for our girls trip! The owner was excellent in responding to all our questions and needs. The views from the home are beautiful. If noise bothers you, this is very close to the airport and there is some type of industrial operation on the river. So you do hear airplanes all night as well as very loud metal banging from the river that starts early in the morning. I only mention this as an FYI! It did not lower the rating for us personally! "
The price is SAR 1,502
SAR 2,780 total
includes taxes & fees
1 Dec - 2 Dec
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

2.0 star property
9.6 out of 10, Exceptional, (12)
"The Chelsea house is a great place to stay. It is a great location to visit Boston. There are some local eateries within walking distance plus a Dunkin Donuts. The house was very clean and had all the amenities you’d need. The bedrooms are on the second and third floors. I would definitely stay here again. "
The price is SAR 619
SAR 1,929 total
includes taxes & fees
2 Dec - 3 Dec
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

Beautiful, Cozy Ultra Convenient Salem Home

8.2 out of 10, Very Good, (32)
"Overall the house was fine. The location was perfect (close to Salem, but the neighborhood was quiet) and the beds were super comfortable. My recommendations would be to have a tv in the first floor living area and tvs in the bedrooms as well. Also some kind of curtain or frosted glass in the upstairs bathroom for privacy, since it looks right out onto the Salem State fields."
The price is SAR 612
SAR 1,141 total
includes taxes & fees
26 Nov - 27 Nov
Beautiful, Cozy Ultra Convenient Salem Home

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (43)
"I stayed here with family members. We thought the property was very lovely and in a pleasant neighborhood. Everything we could need was in the house. We especially appreciated the toiletries and the Nespresso provided. Kitchen was fully functional. The property was very clean and the bedrooms and living spaces were nicely decorated. It felt more personable and comfortable than staying in a hotel. It was truly a nice getaway for us who were in the area to explore Boston!"
Boston's Best Vacation Home

Newly renovated home, top of the line appliances.

9.8 out of 10, Exceptional, (109)
"The house was beautiful, clean, spacious with everything we needed. Loved it."
Newly renovated home, top of the line appliances.

West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!

9.8 out of 10, Exceptional, (49)
"Loved this house! Everything was perfect, easy to communicate with the owner and so clean and lovely!"
West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!

Like a 5 Star hotel

10.0 out of 10, Exceptional, (9)
"The post does the property justice it was exactly what we expected. "
The price is SAR 1,314
SAR 2,204 total
includes taxes & fees
30 Nov - 1 Dec
Like a 5 Star hotel

6 bedroom house in a quiet and convenient neighborhood

6.8 out of 10, (3)
"The good, Large House, lots of bedrooms. Felt very safe, nice Alarm system. And the Piano was very fun for a singing and having fun. Reconstruction in process. The bad, the beds, not good, the house is falling apart, scary stairs, the bath rooms are tiny and do not offer shampoo, conditioner, and conditioner. Could not find bath towels. The ugly - mouse droppings all over the kitchen. Mouse found in one bedroom, captured mouse and took outside. Let host know that there was a mouse and mice...
6 bedroom house in a quiet and convenient neighborhood

Xmas 15% OFF! 37-Greater Boston Cozy Townhouse

9.2 out of 10, Wonderful, (25)
"Jenny/host was quick to answer all of my questions The only negative aspect of our stay was due to the street traffic on Copeland. It made it hard to sleep at times"
The price is SAR 747
SAR 1,602 total
includes taxes & fees
8 Dec - 9 Dec
Xmas 15% OFF! 37-Greater Boston Cozy Townhouse

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

10.0 out of 10, Exceptional, (121)
"The house is located on a quite street near a quaint Downtown Area The house has area for two cars The house was immaculate and very comfortable. The owner Gregg was very welcoming and worked hard to make sure everything was Ok I want to thank him again for letting my family stay in such a beautiful home If you need a place do not hesitate to take this house "
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

Entire Lower Level of the House, Across From The Beach

10.0 out of 10, Exceptional, (11)
"My teenager and I had a great space here. Loved the space and the amenities. Our hosts were amazing people and I never heard them while we were there. The apartment was very clean and cozy, the neighbourhood was adjacent to the ocean, which we loved. Recommending this place to families! We enjoyed our stay. "
The price is SAR 747
SAR 1,338 total
includes taxes & fees
11 Dec - 12 Dec
Entire Lower Level of the House, Across From The Beach

Remodeled Townhouse close to Boston

10.0 out of 10, Exceptional, (22)
"Owner very pleasant & professional for check-in etc. Vey clean apartment inside. Very conveniently located within ~1 mile of I-90 approach, easy access to Cambridge, Boston & surrounding towns but with easier street layout and less hectic traffic in Watertown than some of the other neighborhoods. Can hear a little bit of family in adjacent condo but not too loud. Small bit adequate bathroom. Off-street parking is sufficient. Backyard w patio table neatly maintained. Full kitchen, full-sized...
Remodeled Townhouse close to Boston

Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

10.0 out of 10, Exceptional, (9)
"We really enjoyed our stay at Rose Cottage! There was more than enough room for the 4 of us, and would be great for a family. The amenities were amazing. The kitchen was fully stocked...everything we needed for cooking, a Keurig including k-cups, sugars, creamer (I've never had this included before). A nice little basket of treats awaited us when we arrived. The home is beautifully furnished and decorated. Linda & Glendon were responsive hosts...always getting back to me promptly. A short 15-20...
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

Spacious, New Renovation | Near T

9.4 out of 10, Exceptional, (3)
"So much better than hotel rooms! Traveling with a group of coworkers for a conference we normally have limited time together since we usually have separate hotel rooms. This was an awesome experience that enabled us to spend more time together and get to know each other much better. The house was beautiful and well designed."
Spacious, New Renovation | Near T

Spacious 2BR 2BA Condo & 2x Parking, Minutes from Central Sq, MIT, Harvard.

9.0 out of 10, Wonderful, (11)
"Loved staying here. The place is just as described. Lots of room, each bedroom has its own bathroom. Will be staying here next time we're in town!"
Spacious 2BR 2BA Condo & 2x Parking, Minutes from Central Sq, MIT, Harvard.

MODERN Spacious 4bed 2bath HARVARD MIT BOS Cambridge Somerville walk everywhere!

9.4 out of 10, Exceptional, (43)
"The stay was in suburb of Boston. Good location. There was a few repairs needed. Bathroom sink faucet moved. There was a light in bedroom ceiling that had open wires. Other than that the place was clean. The outside patio could used cleaned up but we didn’t ise"
The price is SAR 1,258
SAR 2,361 total
includes taxes & fees
1 Dec - 2 Dec
MODERN Spacious 4bed 2bath HARVARD MIT BOS Cambridge Somerville walk everywhere!

Waterfront Beach Home With Attached In- Law Suite

10.0 out of 10, Exceptional, (28)
"We all had an awesome stay at this location. The house, neighborhood and host were over the top! Amy stays in touch and provides any information needed pretty quickly. The house has everything 6 adults could need. Plenty of space for more than 6 people, with ample space to have some quiet time alone as well. We felt very safe in the neighborhood and it was good for walking and jogging. The weather was a tad chilly for the middle of Oct for people from FL, NM and ID, but I can imagine how much...
Waterfront Beach Home With Attached In- Law Suite

Perfectly located modern home with smart TVs, high chair, patio, W/D, & AC

9.8 out of 10, Exceptional, (7)
"The family stayed at this home for our Boston start of our Massachusetts vacation. The home was larger than expected and very comfortable. We all enjoyed our time. The only small downfall is the neighborhood is not walkable and a little bit run down, but we felt safe and enjoyed our stay."
Perfectly located modern home with smart TVs, high chair, patio, W/D, & AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chestnut Hill

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (493)
"We enjoyed our stay. It was walkable to Chinatown. Very accessible to subway station. We liked that our room was on the top floor. "
The price is SAR 537
SAR 1,078 total
includes taxes & fees
8 Dec - 9 Dec
Global Luxury Suites Downtown Boston

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (152)
"Everything good "
The price is SAR 496
SAR 937 total
includes taxes & fees
1 Dec - 2 Dec
Maverick Suites at 28 Fenway

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (951)
"It was great. Very clean and especially loved the heating fan in the bathroom. The only thing I’d recommend to enhance the experience would be a more comfortable sofa bed. "
The price is SAR 635
SAR 709 total
includes taxes & fees
2 Dec - 3 Dec
Crescent Suites Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.