Photo by Fun Travelog

Search Cottages in Wellesley

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sep - 14 Sep
In one month
26 Sep - 28 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Cottages in Wellesley

Our top choices for Wellesley cottages

Cozy Pet Friendly House Next To Train
Exterior

Cozy Pet Friendly House Next To Train

2.0 star property
6.8 out of 10, (5)
"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
10.0 out of 10, Exceptional, (1)
The price is SAR 1,343
SAR 1,862 total
includes taxes & fees
8 Sep - 9 Sep
Pet-friendly Home w/ Spacious Yard in Avon!
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!
16 Mi to Boston: Home w/ Deck in Weymouth
House (3 Bedrooms) | Front of property

16 Mi to Boston: Home w/ Deck in Weymouth

3.0 star property
16 Mi to Boston: Home w/ Deck in Weymouth
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!
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
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
House (1 Bedroom) | Interior

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!
House (3 Bedrooms) | Interior

Belmont Home < 3 Mi to Harvard Square!

3.0 star property
Belmont Home < 3 Mi to Harvard Square!
Beautiful Lakeside Milford Family Home & Deck
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Beautiful Lakeside Milford Family Home & Deck

3.0 star property
Beautiful Lakeside Milford Family Home & Deck
Peaceful Getaway Cottage on grounds of historic mid-century gem
Pool

Peaceful Getaway Cottage on grounds of historic mid-century gem

3.0 star property
Peaceful Getaway Cottage on grounds of historic mid-century gem
Great little cottage sitting behind the main house on 4 acres of property.
Property grounds

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.
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!
2 Mi to Gillette Stadium: Foxborough Retreat!
House (4 Bedrooms) | Interior

2 Mi to Gillette Stadium: Foxborough Retreat!

3.0 star property
2 Mi to Gillette Stadium: Foxborough Retreat!
Charming Beach Cottage
Interior

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

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
Property grounds

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

Entire near Boston Cottage House: MBTA, T, all major roads, parking
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wellesley Hotel Reviews

Frequently asked questions

Why book your cottage in Wellesley with Expedia?
We think that vacays should be a breeze, so if you're seeking cottages in Wellesley at a competitive price, Expedia delivers. Keep costs down and go for a low-cost option far from the rush of the city, or book an upmarket cottage to treat your loved ones.
How can I find cheap cottages in Wellesley?
Expedia is here to help you easily locate cheap cottages in Wellesley. To discover your ideal stay in a few quick clicks, try out the filter tool to tailor your search results by amenities, budget and star rating.