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Winchester, MA Holiday Rentals, Apartments and Villas
Holiday Rentals
USA
Massachusetts (MA)
Winchester, MA Holiday Rentals, Apartments and Villas
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Winchester
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Internet or Wifi (46)
Air Conditioning (43)
Washer/Dryer (34)
Other outdoor space (17)
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Suitability
Kid friendly (40)
Pet friendly (12)
Smoking allowed (2)
Wheelchair access (0)
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Holiday Rental House (23)
Condominium/Apartment (23)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Private Chef (0)
Private Beach (0)
Waterfront (0)
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Distance from
5 km
Wright-Locke Farm
Griffin Museum of Photography
Winter Pond
Next Door Theater
Winchester Cultural District
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46 rentals
in Winchester.
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
31
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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House on A+ school area w/AC & W/D
4
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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The following properties within 32 kms of Winchester match all your filters:
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.
37
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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A charming modern suburban 3 bedroom condo close to Boston
18
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 8
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Perfect Stoneham Getaway Just Minutes to Boston!
7
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Charming 1 BR private entrance apt commuters dream
4
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Unique loft style garden level studio apartment
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Cheerful 1-bedroom New England Ranch
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Located north of Boston/ comfort and relaxation in your home away from home
18
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Cozy 2 bedroom Medford
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 5
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Melrose two bedroomer
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Quiet Family Neighborhood
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Your Cozy 1 BR Apt & Relaxing Retreat
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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★Modern Studio-Private Entrance,Washer+Dryer★
7
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Stylish Studio - ✓Sanitized ✓Private ✓Spotless
3
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Beautiful, family-friendly home with yard and patio near Tufts, 10 min to Boston
3
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Charming 2 bedroom Townhome w/private office suite
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 2
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Modern Two Bedroom Condo - Near Boston
12
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
10
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Unique Cathedral Ceiling Condo W/D, Parking
7
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Home away from home for work or graduate school.
5
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 5
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Family-friendly House in Quiet Neighborhood, 5 miles away from Boston!
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 5
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Modern Three Bedroom Condo - Near Boston
4
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 8
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Designer Style 3Br, King Bed, W/D,Parking,Spotless
20
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Spacious Luxury 3 BR ✓Spotless ✓W/D ✓Parking
8
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Home in Woburn - Family + Pet Friendly!
5
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 6
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New 5B3B Single Family with Central AC
16
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Luxury home minutes from downtown, casino, and Tufts university
2
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
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Cozy Lexington MA Home, Spacious, Backyard, Pet & Child Friendly, Free Parking
1
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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597- SPRING GETAWAY EARLY BIRD 10% OFF! Spacious, cozy 5BR apartment in Medford
2
Condo/Apartment
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5 bedrooms
2 bathrooms
Sleeps 6
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Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Chic Queen size bedroom with AC, WiFi in Serene Medford next to Beautiful parks
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Spotless and Modern Apt w/2Ba,W/D,King Bed,Parking
1
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Cozy 4-bedroom house in superb Woburn with WiFi, AC - 16 mins to Boston
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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ChicStylish Near Tufts/Boston 1BR w/ SitStand Desk
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Funky and cozy home ! A little bit of everything for everyone.
3
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
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Bright and Spacious Sleek Studio w/Private Entrance, W/D & Parking
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Modern Near Tufts & Boston 2BR w/ Office & Peloton
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
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Tufts 4BD/2BA - 5.MIN to Harvard&Boston / Free Parking / Walk to Subway
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 12
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Tufts 2br w/ Standing Desk & Home Theater
1
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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5 Mi to TD Garden: Quiet Medford Getaway!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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Stunning Urban Haven
1
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Cozy Self Contain Basement Apartment Close to Boston in a Serene Environment
1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Charming Queen Anne Victorian in Excellent Location, 3 bedrms, office, WIFI&More
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Garden Studio, access to I-93 to Airport, Tufts U, Hiking & Chevalier Theater.
11
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Enchanting Hidden Door Escape
6
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 10
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1
Showing results 1-46 of 46
Frequently Asked Questions about Winchester
Do any holiday rentals in Winchester have a pool?
Yes, here are some popular holiday rentals in Winchester that have a pool:
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
House on A+ school area w/AC & W/D
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.
See all holiday rentals with a pool in Winchester on Tripadvisor
Do any holiday rentals in Winchester have internet access?
Yes, here are some popular holiday rentals in Winchester that have internet access:
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
House on A+ school area w/AC & W/D
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.
See all holiday rentals in Winchester on Tripadvisor
What are the best pet friendly rentals in Winchester?
The best pet friendly rentals in Winchester are:
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
House on A+ school area w/AC & W/D
A charming modern suburban 3 bedroom condo close to Boston
See all pet friendly holiday rentals in Winchester on Tripadvisor
What are some great rentals in Winchester that are kid friendly?
Some of the most popular kid friendly rentals in Winchester are:
Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93
House on A+ school area w/AC & W/D
Quiet Neighborhood, Close to T, Free Wifi, Cable. Washer & Dryer, A/C, Hiking.
See all kid friendly holiday rentals in Winchester on Tripadvisor
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