Winchester fishing vacation rentals
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cottage in Bernardston
4.88 out of 5 average rating, 282 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.
Feb 15 – 22
Apartment in Dublin
4.96 out of 5 average rating, 177 reviewsPrivate Dublin apartment nestled in the woods
Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.
Aug 31 – Sep 7
Apartment in Greenfield
4.96 out of 5 average rating, 257 reviewsMohawk Trail View/ private apt. no cleaning Fee
Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen bed & desk. Apt. Is 2 min's to Rt. 2 Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes.
Jul 23 – 30
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Lake side house rentals in Winchester
Home in Winchendon
4.8 out of 5 average rating, 138 reviewsWaterfront home 2 bedrooms withdeck beach and dock
Jun 21 – 28
Home in Putney
4.84 out of 5 average rating, 118 reviewsSpacious Loft with View
Oct 5 – 12
Home in Athol
4.92 out of 5 average rating, 132 reviewsBig Post and Beam Lake House
Jan 15 – 22
Home in Mont Vernon
4.96 out of 5 average rating, 131 reviewsSerenity on the Pond ~ Private Waterfront, Hot Tub
Sep 6 – 13
Home in Westminster
4.87 out of 5 average rating, 111 reviewsLakefront; view of ski mtn, firepit, dock, kayaks
Dec 7 – 14
Home in Wilmington
4.94 out of 5 average rating, 239 reviewsWilmington. Easy walk to center of town.
May 15 – 22
Home in Winhall
4.9 out of 5 average rating, 183 reviewsA+ Stratton shuttle, Hot Tub, Sauna, 2 masters
Jun 13 – 20
Home in Sunapee
4.98 out of 5 average rating, 126 reviews@SunapeeSeasons—Across from Dewey Beach, Lake View
Nov 24 – Dec 1
Home in Oakham
5.0 out of 5 average rating, 145 reviewsLovely & Peaceful Waterfront Vacation Retreat
Dec 9 – 16
Home in Westminster
4.93 out of 5 average rating, 117 reviewsWachusett Mountain Get-Away
Jan 3 – 10
Home in Dunbarton
4.97 out of 5 average rating, 157 reviewsPicturesque Dunbarton Waterfront Cottage
Apr 9 – 16
Home in Lempster
4.96 out of 5 average rating, 120 reviewsBeautiful waterfront lake house, four season home
Sep 5 – 12
Winchester fishing house rentals
Home in Chesterfield
4.95 out of 5 average rating, 40 reviewsThe River House
Sep 7 – 14
Home in West Brattleboro
4.91 out of 5 average rating, 32 reviewsBeautiful nature retreat minutes to Brattleboro
May 12 – 19
Home in Spofford
5.0 out of 5 average rating, 8 reviewsA-Frame Cottage at Lake Spofford
Oct 1 – 8
Home in Orange
4.95 out of 5 average rating, 21 reviewsThe Zen Waterfront Retreat: A Sweetwater Stay
Jun 11 – 18
Home in Orange
4.94 out of 5 average rating, 49 reviewsFour Season Cozy Lake House
Sep 2 – 9
Home in Rindge
5.0 out of 5 average rating, 80 reviewsWaterfront escape
Sep 8 – 15
Home in Rindge
4.9 out of 5 average rating, 21 reviewsMagic Lakehouse, Waterfront, Private Beach & Dock
Sep 26 – Oct 3
Home in Belchertown
5.0 out of 5 average rating, 16 reviewsMoonstone n' Lucy's Lake House – romantic, serene
Mar 21 – 28
Home in Ashburnham
4.92 out of 5 average rating, 36 reviewsLake House with Island and boats!
Mar 1 – 8
Home in Shutesbury
4.95 out of 5 average rating, 19 reviewsLakeside 2 Bedroom House
Dec 13 – 20
Home in Orange
4.9 out of 5 average rating, 67 reviewsMike's Lake House
Apr 22 – 29
Home in Alstead
5.0 out of 5 average rating, 17 reviewsThe Lake House
May 25 – Jun 1
Other great vacation rentals in Winchester
Cabin in Brattleboro
4.89 out of 5 average rating, 441 reviewsCottage
Aug 14 – 21
Cottage in Orange
4.95 out of 5 average rating, 128 reviewsThe Lake Cottage: A Sweetwater Stay
Oct 9 – 16
Home in Chesterfield
4.97 out of 5 average rating, 225 reviewsCharming Country Home
Mar 9 – 16
Cottage in Petersham
4.99 out of 5 average rating, 146 reviewsCider House Cottage
Nov 6 – 13
Barn in Marlboro
4.95 out of 5 average rating, 260 reviewsThe Studio With a View. Bring your dog, too!
Oct 16 – 23
Apartment in Brattleboro
4.89 out of 5 average rating, 313 reviewsQuiet St in Town, gardens, terrace
Apr 26 – May 3
Guesthouse in Brattleboro
4.99 out of 5 average rating, 197 reviewsLight Filled Loft in the Vermont Countryside
Apr 20 – 27
Apartment in Marlboro
4.94 out of 5 average rating, 220 reviewsShakespeare’s Folly Side Farm and AirBnB.
Sep 5 – 12
Tiny home in Brattleboro
4.95 out of 5 average rating, 173 reviews"Mountain View" Hike In Cabin Retreat
Aug 24 – 31
Barn in Chester
4.99 out of 5 average rating, 487 reviewsInviting studio apartment above barn in Vermont
Apr 24 – May 1
Guesthouse in Fitzwilliam
4.86 out of 5 average rating, 331 reviewsTranquil Guest House with Sauna
Dec 29 – Jan 5
Cabin in Guilford
4.96 out of 5 average rating, 476 reviewsSerenity Now - Couples Retreat or Writer's Dream
Oct 25 – Nov 1
Destinations to explore
- Cambridge Vacation rentals
- Salem Vacation rentals
- Lake George Vacation rentals
- Providence Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Québec City Vacation rentals
- Québec Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom