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Wellesley Vacation Rentals

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Browse Select Wellesley Vacation Homes

CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA
Beach
CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA
2.0 star property
9.0 out of 10, Wonderful, (6)
"We stayed for a short trip for a concert, and it worked out great! The space was very comfortable and clean, and was very conveniently located! Would stay again!"
CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA
Modern home-like 3BR2BA Retreat/Minutes to T
Fridge, microwave, oven, stovetop
Modern home-like 3BR2BA Retreat/Minutes to T
9.6 out of 10, Exceptional, (8)
"Beautiful and spotless (and I mean spotless) 2nd floor apartment. Easy check in/out. Easy street parking on weekends (Friday after 7pm through Monday 7am) for non-residents. Property owner lives 2 blocks away and is easy to reach by phone or messaging through the Vrbo app. One of the smoke detectors kept inadvertently going off as soon as we arrived. I messaged the owner, who replied back and showed up in less than five minutes. One note (that has nothing to do with the space), when we...
The price is CA $511
CA $1,026 total
includes taxes & fees
Sep 30 - Oct 1
Modern home-like 3BR2BA Retreat/Minutes to T
Copley House - 1 Bedroom Suite
TV
Copley House - 1 Bedroom Suite
8.8 out of 10, Excellent, (3)
"Great property, small efficiency style apartment. Great location, great neighborhood. Parking in the 35 Westland Garage."
The price is CA $445
CA $575 total
includes taxes & fees
Sep 30 - Oct 1
Copley House - 1 Bedroom Suite
1918 Family Home near Boston
Fridge, microwave, oven, stovetop
1918 Family Home near Boston
10.0 out of 10, Exceptional, (24)
"We loved staying here! Convenient to Boston and Cambridge. Fully equipped kitchen. Best for up to six."
1918 Family Home near Boston
Revere Luxury House ,private beach
Microwave, oven, stovetop, dishwasher
Revere Luxury House ,private beach
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 CA $472
CA $860 total
includes taxes & fees
Sep 29 - Sep 30
Revere Luxury House ,private beach
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fridge, microwave, oven, stovetop
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
10.0 out of 10, Exceptional, (50)
"Beautiful property in a nice location. 10 min to Fenway, 40 min walk to downtown. Suggested property improvements, bedroom lighting, shower water pressure and hot water"
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Union Square House
Outdoor dining
Union Square House
9.6 out of 10, Exceptional, (57)
"My family and I were in for a wedding and this turned out to be literally around the corner from the venue. The location was convenient, but also in a lovely part of town. The house itself is a mix of dated construction and modern upgrades. The bathroom, in particular, is quite comfortable. On the flip side, the stairs going up to the top floor bedrooms are very, very steep. "
Union Square House
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Aerial view
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
9.6 out of 10, Exceptional, (70)
"Friends weekend, we had a blast and loved the house. "
The price is CA $539
CA $999 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Wonderful Renovated Family Friendly Home Close to Boston and Lexington
Exterior
Wonderful Renovated Family Friendly Home Close to Boston and Lexington
10.0 out of 10, Exceptional, (54)
"Had a great time here. Nice neighbor and plenty of groceries store, restaurants close by. The owner gets right back promptly with any questions or concerns. Overall exceptional house would highly recommend. ☺️"
Wonderful Renovated Family Friendly Home Close to Boston and Lexington
Football Fans Lake Retreat - 5 Mins to Gillette!
Flat-screen TV
Football Fans Lake Retreat - 5 Mins to Gillette!
10.0 out of 10, Exceptional, (67)
"We all loved this property and thought it was the most appointed rental we have stayed in. Everything you need and more, lots of space to sleep 10 comfortably, kitchen is the right size and to have a table where we could all sit and eat together was the BEST! "
Football Fans Lake Retreat - 5 Mins to Gillette!
Modern Smart Home with EV charger Near Boston & Harvard, 0.7 miles to MBTA
Property grounds
Modern Smart Home with EV charger Near Boston & Harvard, 0.7 miles to MBTA
9.8 out of 10, Exceptional, (10)
"We had a very pleasant stay. The house is very clean and very well kept. The location is convenient to neighborhood food or drink shopping. We can feel the host makes real efforts to make the place comfortable for its guests. The open floor plan makes the place very welcoming for family or friend get together. The host is also very responsive to questions relating to our stay before and after our arrival. We would recommend this place ."
Modern Smart Home with EV charger Near Boston & Harvard, 0.7 miles to MBTA
Charming 4-bedroom house in delightful Marlborough with AC, WiFi
Property grounds
Charming 4-bedroom house in delightful Marlborough with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (1)
"Really big house in a quite area "
The price is CA $678
CA $1,636 total
includes taxes & fees
Oct 27 - Oct 28
Charming 4-bedroom house in delightful Marlborough with AC, WiFi
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs
Terrace/patio
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs
7.0 out of 10, Good, (18)
"It's in a basement and there was a door to another part of the basement that was locked and we could see a light that was on all night on the other side. It was very quiet though, great if you just need somewhere to sleep."
The price is CA $94
CA $166 total
includes taxes & fees
Sep 29 - Sep 30
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs
Boston's Best Vacation Home
Exterior
Boston's Best Vacation Home
9.8 out of 10, Exceptional, (35)
"It was a cute home away from the busy Boston area. Roomy and clean. Bed sheets were so soft! Owners were great to work with and didn't need to bother them either. Highly recommend!"
Boston's Best Vacation Home
West End Deluxe Suite -Book 1 Week and SAVE up to 20% Long term stays welcome!
Interior
West End Deluxe Suite -Book 1 Week and SAVE up to 20% Long term stays welcome!
9.8 out of 10, Exceptional, (46)
"Three friends met up for a long weekend of fun in Boston. The property is located near BC, not too far from downtown Boston and Logan Airport. The host Susan quickly addressed any needs we had. Fun trip and solid rental. I stay there again the next time I’m in the area."
West End Deluxe Suite -Book 1 Week and SAVE up to 20% Long term stays welcome!
✨Private Studio w/ Loft Center Historic Carlisle✨
Exterior
✨Private Studio w/ Loft Center Historic Carlisle✨
9.6 out of 10, Exceptional, (16)
"The space was clean and comfortable. It's on a somewhat busy road but it's not too loud. The bed was very comfortable. The only downside was that there's no way to do any cooking, there's only a mini fridge and a microwave. There's not a toaster or even a cutting board for chopping fruit/veggies. Besides this, it was an easy and comfy stay."
The price is CA $195
CA $299 total
includes taxes & fees
Oct 14 - Oct 15
✨Private Studio w/ Loft Center Historic Carlisle✨
Boston's Beach Home: Pool, 1min to Beach, Pet +
Fridge, microwave, oven, stovetop
Boston's Beach Home: Pool, 1min to Beach, Pet +
10.0 out of 10, Exceptional, (2)
"This was our first time renting a whole house. I wanted a space that the family could all be together instead of multiple hotel rooms. This house was perfect. We had 6 adults in the house and there was plenty of space. The kitchen island was huge and perfect for preparing meals and chatting with the family. The dinning room table was perfect for eating and playing games. We also played pool, watched TV using our Apps (which we enjoy so much better than cable), and relaxed. The location was...
Boston's Beach Home: Pool, 1min to Beach, Pet +
Remodeled Townhouse close to Boston
Private kitchen
Remodeled Townhouse close to Boston
9.8 out of 10, Exceptional, (20)
"We had a lovely time staying at your home. It was very close to the Boston area and very convenient for us for our stay."
Remodeled Townhouse close to Boston
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
Living area
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
10.0 out of 10, Exceptional, (5)
"Excellent location, great safe and quiet neighborhood, lots of local flare, READ THE instructions BINDER when you arrive for GREAT TIPS, outstanding hosts, house is comfortable and well appointed, park your car and take the train to the city. I rented a car because I wanted to visit the coastal cities, Cape Code, Provincetown etc., otherwise no car is needed. Great band for the buck!"
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
New 5B3B Single Family with Central AC
Exterior
New 5B3B Single Family with Central AC
9.8 out of 10, Exceptional, (17)
"Great place to stay. A little short on towels, plates and kitchen seating for a place that sleeps 10, but the hosts were very communicative and everything was as advertised. Easy drive into downtown Boston for our family vacation. Recommend!"
New 5B3B Single Family with Central AC
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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 Wellesley

Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area
Maverick Suites at 28 Fenway
2.5 star property
9.2 out of 10, Wonderful, (123)
"It was in a good location for walking Boston. "
The price is CA $178
CA $336 total
includes taxes & fees
Sep 29 - Sep 30
Maverick Suites at 28 Fenway
HYATT house Boston/Burlington
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2281)
"Just a standard hotel for a quick stay (nothing special). I found it a little annoying to have to pay for parking, even though it’s only $10 a night….. it’s Burlington with parking everywhere not downtown Boston. "
The price is CA $241
CA $270 total
includes taxes & fees
Sep 29 - Sep 30
HYATT house Boston/Burlington
Temple Place Suites
Deluxe Studio
Temple Place Suites
2.5 star property
6.8 out of 10, (146)
"Location is everything! Clean and comfortable and exactly as advertised "
The price is CA $183
CA $285 total
includes taxes & fees
Sep 30 - Oct 1
Temple Place Suites
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.