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Compare 29 Cottages in Winchester with updated reviews, rates, and availability.

The Shore House, steps to the ocean meet crisp clean beach side retreat!

8.8 out of 10, Excellent, (3)
"The house was quite lovely. We were expecting 2 rooms with twin beds but there was just 1 room with twin beds. Downstairs space was great. We were surprised that there wasn’t an outdoor space to barbecue and have dinner for a group. Deck was small so great for coffee but not a meal at the end of the day. There were some beach towels and bath towels but we expected more towels. AC worked well. The 1 bathroom was small. It would have helped to at least have an outdoor shower. For the price of our...
The Shore House, steps to the ocean meet crisp clean beach side retreat!

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

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

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

10.0 out of 10, Exceptional, (3)
"We stayed here for 5 weeks. I had no idea when I booked it how amazing it would be. My kids say it was the best summer ever. The cottage is so cute. The location is amazing and all the amenities are amazing. They cottage community has so many activities going all the time, the beach and lake are so fun with a dock you can swim to, there is a restaurant on the weekends, riding the gold cart around, the swimming pool… I can’t say enough good about this place! I wish I owned one. Don’t hesitate to...
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat

Beach & pond Cottage

9.6 out of 10, Exceptional, (5)
"The cottage was well laid-out for a small to medium size family to stay. Golf cart was great for taking small children to nearby water features (swimming pools and lake). Other visitors and local residents were very friendly and courteous. Perfect place for a week away from hectic city life."
Beach & pond Cottage

Waterfront Cottage in Summer Village w/ Grill

2.5 star property
Waterfront Cottage in Summer Village w/ Grill

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

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

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!

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 Views: Historic Marblehead Home

3.0 star property
Waterfront Views: Historic Marblehead Home

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

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

Gated Resort Community

Gated Resort Community

Summer Village Family Cottage w/ Community Perks!

2.0 star property
Summer Village Family Cottage w/ Community Perks!

Waldingfield - Pool House / Sleeps 2

10.0 out of 10, Exceptional, (1)
"This property is a gem! It made for a perfect weekend getaway with my fiance. The pool house is just right for 2 people and the grounds are simply lovely. Edwin was a great host, providing a tour and lots of info about the area. I would stay here again in a heartbeat!"
Waldingfield - Pool House / Sleeps 2

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!

Luxe 4BR 3 Bath North End & Faneuil Hall

3.0 star property
Luxe 4BR 3 Bath North End & Faneuil Hall
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 Winchester

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (425)
"The checkin and room key code access process is a little weird with needing to use an an app or complete it on their website, but other than that, it was a pleasant stay in a convenient part of town."
The price is AED 473
AED 548 total
includes taxes & fees
2 Feb - 3 Feb
Sonder 907 Main

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (860)
"It was a great location, clean and affordable "
The price is AED 509
AED 600 total
includes taxes & fees
26 Feb - 27 Feb
No. 284 powered by Sonder

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very Good, (524)
"It’s set up like an air b and b so the kitchen was really nice for our group"
The price is AED 363
AED 863 total
includes taxes & fees
5 Feb - 6 Feb
Global Luxury Suites 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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