Winchester vacation rentals

From simple studios to luxe lofts, find vacation rentals that are right for you on Airbnb.

Vacation rentals in Winchester

₹13453 Private Villa 15 mins from Boston
41 reviews

15 minutes away from downtown Boston and Cambridge. Spacious single family home with 4+ bedrooms and 3 bathrooms. 3,600 +sqft of living space. Private parking for 5+ cars. Q... read more
₹4665 Nice apartment in Winchester
32 reviews

Fourth floor apartment has beautiful view of hillside and a duck pond. Quiet and peaceful neighborhood is 15 minutes out of Boston. Supermarket, restaurants, and nature reserv... read more
₹5408 King bedroom close to public transp
16 reviews

My home is within walking distance of historic Winchester with art and culture, great views, shops, restaurants and bars. The location is close to Boston; just 5 minute walk to ... read more
₹8451 Quiet, modern and clean apartment
11 reviews

Newly renovated space with new furnishings. Short walk to downtown Winchester with many restaurants, cafes and shops, bus line at end of road, commuter rail-with short train ri... read more
₹6422 In-law-apartment close to Boston
10 reviews

This is our basement in-law-apt. with a private entrance, kitchen and full bathroom. We are located in Winchester, MA and have a 15 minute walk to downtown Winchester and the co... read more
₹28732 Swimspa, outdoor fireplace, AC, DISCOUNTS!
6 reviews

Conveniently located less than 10 miles from downtown Boston and next door to historic Lexington, in the hilly section of Winchester, this house offers a spa-like retreat while ... read more

Favorite Winchester vacation rentals

₹5070 Private bedroom in Winchester
2 reviews

My place is close to Boston, parks, and public transport. You’ll love my place because of the location. My place is good for solo adventurers and business travelers. A private ... read more
₹4056 Single room close to public transpo
4 reviews

My place is good for solo adventurers and business travelers. It is 8 minutes walk to the Wedgemere train station (Lowell/North Station line) and 4 minutes walk to the local bus... read more
₹35492 Luxury 6 BR, 4.5 BA, hot tub, 110" TV, gardens
2 reviews

Luxury, spacious so close to downtown Boston! Just 8 miles (15 minutes) north of Beacon Hill and Back Bay. Perfect for a multi-generation family gathering, vacation get-away, ... read more
₹3380 Bedroom(s) + Bath in Boston Suburb House
3 reviews

Large house with 3 bedrooms available. Price listed is for Bedroom 1 only (contact me for other rooms' prices). One master suite available upon request with its private bathroom... read more
₹3380 Bedroom available in large boston suburban house
2 reviews

This is bedroom 2 (located in the same house in my other listing). Downstairs there is kitchen, living room with TV (and cable) and dining room available. A large backyard, quie... read more
₹7098 Beautiful 3BR in a quiet neighborhood
2 reviews

New to the listing. Our beautifully renovated house is super clean and situated in a beautiful quiet neighborhood of Winchestser. Convenient location to visit Boston, Cambridge,... read more

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