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Featured Cottages in Wellesley and around

Cozy Pet Friendly House Next To Train

2.0 star property
6.6 out of 10, (4)
"It was a sad trip as we were dropping our daughter off for college. So it was a blessing to have this central location to be easy to check into to, keep clean, and feel safe. We were spooked out at the basement it that’s cause we do not have basements where we live. We let the horror stories about basements get the better of us. But that lasted like 60 minutes. Haha. I would rent this again. "
Cozy Pet Friendly House Next To Train

COZY, MODERN, Charming Cottage 1min to the beach

9.0 out of 10, Wonderful, (7)
"This little cottage has a perfect location on Wollaston Beach right behind Tony’s Clam Shop. Walking distance to the water as well as a playground for kiddos. Back yard is fairly nice but not fenced and had some glass and nails about, so keep shoes on the little ones! Though hosts were otherwise prepared with a pack and play and high chair, which our family appreciated juggling multiple babies for the family reunion. Kitchen was great to cook in and the back porch was lovely for morning coffee...
COZY, MODERN, Charming Cottage 1min to the beach

Waterfront Retreat w/ Deck ~ 7 Mi to Boston!

3.0 star property
8.0 out of 10, Very good, (1)
"Comfortable place to stay on the water overlooking Boston Harbor and downtown. Sunsets are amazing behind the tall buildings of downtown. Trails close by for walking and sightseeing. Nice kitchen and bathrooms. We had trouble with getting any of the TV's to work and there was an annoying flood light shining on the back deck from the neighbors house all day and night. Other than those two things it was nice to have a house on the water with a fantastic view. "
Waterfront Retreat w/ Deck ~ 7 Mi to Boston!

Classic Waterfront Home on Lake Maspenock w/ Grill

3.0 star property
Classic Waterfront Home on Lake Maspenock w/ Grill

Bright & Pet-friendly Home: 2 Mi to Harvard Square

3.0 star property
10.0 out of 10, Exceptional, (1)
Bright & Pet-friendly Home: 2 Mi to Harvard Square

Private Island Retreat on Lake Pearl

Private Island Retreat on Lake Pearl

Great little cottage sitting behind the main house on 4 acres of property.

Great little cottage sitting behind the main house on 4 acres of property.

Entire near Boston Cottage House: MBTA, T, all major roads, parking

Entire near Boston Cottage House: MBTA, T, all major roads, parking

Beautiful Lakeside Milford Family Home & Deck

3.0 star property
Beautiful Lakeside Milford Family Home & Deck

Charming Beach Cottage

10.0 out of 10, Exceptional, (1)
"Great location. Lovely island. Property has great view of the water from the enclosed patio. Everything inside is state of the art, from security to lighting and audio/video. Has everything you need and is not a hotel. We will come back."
Charming Beach Cottage

Weymouth Waterfront Getaway w/ Hot Tub & Pool!

3.0 star property
Weymouth Waterfront Getaway w/ Hot Tub & Pool!

Pet-friendly Revere Getaway, Steps From the T!

3.0 star property
Pet-friendly Revere Getaway, Steps From the T!

Charming Boston Area Home < 1 Mi to Revere Beach!

3.0 star property
Charming Boston Area Home < 1 Mi to Revere Beach!

Football Fans Lake Retreat - 5 Mins to Gillette!

3.0 star property
Football Fans Lake Retreat - 5 Mins to Gillette!

Pet-friendly Lynn Home w/ Patio - 3 Mi to Beach!

3.0 star property
Pet-friendly Lynn Home w/ Patio - 3 Mi to Beach!

Waltham Vacation Rental ~ 12 Mi to Downtown Boston

3.0 star property
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
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

Sonder 907 Main

4.0 star property
8.2 out of 10, Very good, (433)
"The property was close to anything you could need and all processes were beyond easy. Having all access on your phone was amazing. "
The price is €142
includes taxes & fees
18 Feb - 19 Feb
Sonder 907 Main

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (868)
"my favorite stay ever. i loved my stay and everything about it and can’t wait to come back soon. "
The price is €173
includes taxes & fees
24 Feb - 25 Feb
No. 284 powered by Sonder

Temple Place Suites

2.5 star property
6.8 out of 10, (182)
"Insane lil spot for seeing Boston and surrounding areas!"
The price is €158
includes taxes & fees
18 Feb - 19 Feb
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.

Frequently asked questions

Why book your cottage in Wellesley with Expedia?
Reserving a cottage in Wellesley is as easy as deciding on your travel dates and selecting your ideal place for a getaway in nature. From chic retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all styles and tastes. As for the best deals around? We have them too!
How can I find cheap cottages in Wellesley?
The quickest way to find cheap cottages in Wellesley is with Expedia’s handy filter tool. Narrow down your search results by star rating, amenities and budget to snag unbeatable bargains in a few clicks.
What is there to do in Wellesley near my cottage?
After you’ve unpacked your bags and settled in, head out and explore the cool things Wellesley has on offer. Wellesley College is a great attraction to add to your travel itinerary.