Photo by Fun Travelog

Holiday Homes in Wellesley

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Wellesley

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 AU$394
includes taxes & fees
17 Dec - 18 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 AU$455
includes taxes & fees
1 Dec - 2 Dec
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 AU$1,150
includes taxes & fees
3 Dec - 4 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 AU$797
includes taxes & fees
3 Dec - 4 Dec
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

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 AU$915
includes taxes & fees
1 Dec - 2 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

Revere Luxury House ,Private Beach

2.0 star property
6.0 out of 10, (2)
"We travel in a 45' Coach. Could not find a RV Park for the week-end. This unit was available and a perfect fit for our time in Boston. "
The price is AU$788
includes taxes & fees
1 Dec - 2 Dec
Revere Luxury House ,Private Beach

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 AU$624
includes taxes & fees
11 Dec - 12 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.

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 were in Everett for our daughter's wedding nearby. This is a beautiful spacious home with everything we needed and more. Plenty of towels, a stocked coffee and tea area, ample kitchen supplies for cooking, a washer & dryer, large refrigerator, plenty of living space, very comfortable beds and 3!! bathrooms. So organized with everything labeled. Check-in was a breeze and check-out was minimal and easy. Highly recommend. 10 stars."
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

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 AU$982
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

Xmas 15% OFF! 39-Newly Built & Cozy Townhouse

9.8 out of 10, Exceptional, (37)
"Super clean, large spacious house. Beautiful updated kitchen and bathrooms. Exceeded our expectations…..Would definitely recommend. "
The price is AU$262
includes taxes & fees
5 Dec - 6 Dec
Xmas 15% OFF! 39-Newly Built & Cozy Townhouse

Waterfront Lake house near Gillette Stadium and central to Boston and Providence

10.0 out of 10, Exceptional, (8)
"Wonderdul location. Close to shopping, foxboroigh, restaurants. "
Waterfront Lake house near Gillette Stadium and central to Boston and Providence
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.
Don't see what you're looking for?
See all available properties in Wellesley
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Wellesley

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 AU$415
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)
"Great stay. "
The price is AU$293
includes taxes & fees
29 Dec - 30 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 AU$290
includes taxes & fees
3 Dec - 4 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.