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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 32 Cottages in Winchester with updated reviews, rates, and availability.

NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Interior

NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room

3.0 star property
10.0 out of 10, Exceptional, (9)
"We stayed at this lovely cottage on our trip to Salem,Ma and it is conveniently located within about 20 mins to Salem. While we were not visiting Salem we ventured around Gloucester and visited many delicious restaurants and viewed the ocean. 10/10 recommend and look forward to coming back!"
NEW -Lakefront 2 Bed / 3 bath + Extra Bed off of living room
Pond Access: Waterfront Littleton Hideaway!
Fridge, microwave, stovetop, coffee/tea maker

Pond Access: Waterfront Littleton Hideaway!

Pond Access: Waterfront Littleton Hideaway!
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
Pool

Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site

2.0 star property
10.0 out of 10, Exceptional, (1)
"My wife literally did not want to leave John's cottage at Summer Village. John updated and his wife tastefully decorated their cottage and thought of everything including spices, toiletries, swim toys and a fully stocked kitchen allowing for great home cooked meals. The location is very quiet and private abutting a nature preserve and the neighbors were friendly and welcoming. We swam in the pool and played on the beach every day. John promptly answered any questions we had and offered...
Charming 2-bedroom cottage in Westford, sandy beach, 2 pools, restaurant on site
COZY, MODERN, Charming Cottage 1min to the beach
Terrace/patio

COZY, MODERN, Charming Cottage 1min to the beach

9.0 out of 10, Wonderful, (7)
"Very charming house in cool location. It was very easy to reach all of Boston's attractions by public transportation with a pleasant walk to the Red Line. This house was the perfect accommodation for our family."
COZY, MODERN, Charming Cottage 1min to the beach
Waterfront Cottage in Summer Village w/ Grill
Interior

Waterfront Cottage in Summer Village w/ Grill

2.5 star property
Waterfront Cottage in Summer Village w/ Grill
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Outdoor pool, a heated pool

Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat

10.0 out of 10, Exceptional, (3)
"Everything was perfect except very minor tv problem. I wil be back."
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Inviting Summer Village Cottage: Golf Cart & More!
Outdoor dining

Inviting Summer Village Cottage: Golf Cart & More!

Inviting Summer Village Cottage: Golf Cart & More!
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Aerial view

Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston

10.0 out of 10, Exceptional, (2)
"Family reunion at our favorite summer place ."
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
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!
Summer Village! Charming 2-bedroom cottage with AC, WiFi in delightful Westford
Aerial view

Summer Village! Charming 2-bedroom cottage with AC, WiFi in delightful Westford

Summer Village! Charming 2-bedroom cottage with AC, WiFi in delightful Westford
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
Interior

Waltham Vacation Rental ~ 12 Mi to Downtown Boston

3.0 star property
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
Waterfront Cottage in Summer Village w/ Grill
Interior

Waterfront Cottage in Summer Village w/ Grill

3.0 star property
Waterfront Cottage in Summer Village w/ Grill
Pet-friendly Revere Getaway, Steps From the T!
Microwave, oven, stovetop, dishwasher

Pet-friendly Revere Getaway, Steps From the T!

3.0 star property
Pet-friendly Revere Getaway, Steps From the T!
10 Mi to Crane Beach: Wooded Home Near Boston!
House (4 Bedrooms) | Interior

10 Mi to Crane Beach: Wooded Home Near Boston!

3.0 star property
10 Mi to Crane Beach: Wooded Home Near Boston!
Belmont Home < 3 Mi to Harvard Square!
Interior

Belmont Home < 3 Mi to Harvard Square!

3.0 star property
Belmont Home < 3 Mi to Harvard Square!
Trail Access On-site: Gorgeous MCM Deck House!
Interior

Trail Access On-site: Gorgeous MCM Deck House!

3.0 star property
Trail Access On-site: Gorgeous MCM Deck House!
Inviting Summer Village Cottage: Golf Cart & More!
Microwave, oven, stovetop, dishwasher

Inviting Summer Village Cottage: Golf Cart & More!

3.0 star property
Inviting Summer Village Cottage: Golf Cart & More!
Waterfront Views: Historic Marblehead Home
Interior

Waterfront Views: Historic Marblehead Home

3.0 star property
Waterfront Views: Historic Marblehead Home
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
Interior

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

3.0 star property
Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub
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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