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Browse Select Wellesley Cottages

Cozy Pet Friendly House Next To Train
Situated on a quiet street, this charming home features a welcoming front porch and a classic two-story design.

Cozy Pet Friendly House Next To Train

2.0 star property
6.6 out of 10, (4)
"My family and I stayed here for 5 days in August and it was lovely! Thanks for everything. The beds were very comfortable and the house was very clean and nice."
Cozy Pet Friendly House Next To Train
Pet-friendly Home w/ Spacious Yard in Avon!
House (4 Bedrooms) | Interior

Pet-friendly Home w/ Spacious Yard in Avon!

3.0 star property
Pet-friendly Home w/ Spacious Yard in Avon!
Trail Access On-site: Gorgeous MCM Deck House!
House (4 Bedrooms) | Interior

Trail Access On-site: Gorgeous MCM Deck House!

3.0 star property
Trail Access On-site: Gorgeous MCM Deck House!
5 Mi to TD Garden: Quiet Medford Getaway!
House (2 Bedrooms) | Interior

5 Mi to TD Garden: Quiet Medford Getaway!

3.0 star property
5 Mi to TD Garden: Quiet Medford Getaway!
Classic Waterfront Home on Lake Maspenock w/ Grill
House (3 Bedrooms) | Interior

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
Situated on a corner lot, this charming house features a gabled roof and a chimney.

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
Waterfront Retreat w/ Deck ~ 7 Mi to Boston!
Enjoy breathtaking views of the bay from this deck overlooking calm waters.

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!
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
House (3 Bedrooms) | Front of property

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

3.0 star property
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
Pet-friendly Revere Getaway, Steps From the T!
House (2 Bedrooms) | Interior

Pet-friendly Revere Getaway, Steps From the T!

3.0 star property
Pet-friendly Revere Getaway, Steps From the T!
Belmont Home < 3 Mi to Harvard Square!
Enjoy a peaceful retreat in a serene backyard with a paved patio, shaded by a large tree and surrounded by a brick wall.

Belmont Home < 3 Mi to Harvard Square!

3.0 star property
Belmont Home < 3 Mi to Harvard Square!
Football Fans Lake Retreat - 5 Mins to Gillette!
House (3 Bedrooms) | Interior

Football Fans Lake Retreat - 5 Mins to Gillette!

3.0 star property
Football Fans Lake Retreat - 5 Mins to Gillette!
Great little cottage sitting behind the main house on 4 acres of property.
Enjoy a backyard with a swimming pool and a traditional house with a gabled roof.

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.
Beautiful Lakeside Milford Family Home & Deck
Relax on the serene deck overlooking the calm lake, with a glass table and two chairs for dining or socializing.

Beautiful Lakeside Milford Family Home & Deck

3.0 star property
Beautiful Lakeside Milford Family Home & Deck
2 Mi to Gillette Stadium: Foxborough Retreat!
Welcome to a charming two-story home with a cozy porch and deck, surrounded by a beautifully maintained lawn and a stone wall.

2 Mi to Gillette Stadium: Foxborough Retreat!

3.0 star property
2 Mi to Gillette Stadium: Foxborough Retreat!
Charming Boston Area Home < 1 Mi to Revere Beach!
Property grounds

Charming Boston Area Home < 1 Mi to Revere Beach!

3.0 star property
Charming Boston Area Home < 1 Mi to Revere Beach!
Charming Beach Cottage
Cozy retreat with a front porch, surrounded by lush greenery and a welcoming entrance.

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
The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC
Relax in this serene outdoor space with a view of the surrounding landscape.

The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC

The Little House. Historic 2-BR waterfront cottage in Winchester w/ WiFi, AC
Entire near Boston Cottage House: MBTA, T, all major roads, parking
Stunning two-story building with a symmetrical facade and evenly spaced windows.

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

Entire near Boston Cottage House: MBTA, T, all major roads, parking
16 Mi to Boston: Home w/ Deck in Weymouth
House (3 Bedrooms) | Interior

16 Mi to Boston: Home w/ Deck in Weymouth

3.0 star property
16 Mi to Boston: Home w/ Deck in Weymouth
Pet-friendly Lynn Home w/ Patio - 3 Mi to Beach!
Exterior

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

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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Renovated rooms and Lobby make this hotel my first choice in Boston"
CARLOS 1-night trip
Posted 20 hours ago
Hilton Boston Park Plaza