Winchester fishing vacation rentals

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Bernardston

4.88 out of 5 average rating, 282 reviews

Cozy, 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

G$24,464 GYD per night
Guest favorite

Apartment in Dublin

4.96 out of 5 average rating, 177 reviews

Private 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

G$23,214 GYD per night
Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 257 reviews

Mohawk 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

G$21,955 GYD per night

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Monadnock Speedway4 locals recommend
The Rustic Table8 locals recommend
Northfield Drive-In Theatre13 locals recommend
A1 Pizza of Winchester5 locals recommend
Kulick's Market7 locals recommend
Win Win Express3 locals recommend

Lake side house rentals in Winchester

Superhost

Home in Winchendon

4.8 out of 5 average rating, 138 reviews

Waterfront home 2 bedrooms withdeck beach and dock

Jun 21 – 28

G$31,072 GYD per night
Superhost

Home in Putney

4.84 out of 5 average rating, 118 reviews

Spacious Loft with View

Oct 5 – 12

G$35,313 GYD per night
Guest favorite

Home in Athol

4.92 out of 5 average rating, 132 reviews

Big Post and Beam Lake House

Jan 15 – 22

G$110,532 GYD per night
Guest favorite

Home in Mont Vernon

4.96 out of 5 average rating, 131 reviews

Serenity on the Pond ~ Private Waterfront, Hot Tub

Sep 6 – 13

G$154,608 GYD per night
Guest favorite

Home in Westminster

4.87 out of 5 average rating, 111 reviews

Lakefront; view of ski mtn, firepit, dock, kayaks

Dec 7 – 14

G$68,153 GYD per night
Guest favorite

Home in Wilmington

4.94 out of 5 average rating, 239 reviews

Wilmington. Easy walk to center of town.

May 15 – 22

G$50,571 GYD per night
Guest favorite

Home in Winhall

4.9 out of 5 average rating, 183 reviews

A+ Stratton shuttle, Hot Tub, Sauna, 2 masters

Jun 13 – 20

G$131,555 GYD per night
Guest favorite

Home in Sunapee

4.98 out of 5 average rating, 126 reviews

@SunapeeSeasons—Across from Dewey Beach, Lake View

Nov 24 – Dec 1

G$72,750 GYD per night
Guest favorite

Home in Oakham

5.0 out of 5 average rating, 145 reviews

Lovely & Peaceful Waterfront Vacation Retreat

Dec 9 – 16

G$125,534 GYD per night
Guest favorite

Home in Westminster

4.93 out of 5 average rating, 117 reviews

Wachusett Mountain Get-Away

Jan 3 – 10

G$52,522 GYD per night
Guest favorite

Home in Dunbarton

4.97 out of 5 average rating, 157 reviews

Picturesque Dunbarton Waterfront Cottage

Apr 9 – 16

G$59,466 GYD per night
Superhost

Home in Lempster

4.96 out of 5 average rating, 120 reviews

Beautiful waterfront lake house, four season home

Sep 5 – 12

G$120,142 GYD per night

Winchester fishing house rentals

Guest favorite

Home in Chesterfield

4.95 out of 5 average rating, 40 reviews

The River House

Sep 7 – 14

G$35,201 GYD per night
Guest favorite

Home in West Brattleboro

4.91 out of 5 average rating, 32 reviews

Beautiful nature retreat minutes to Brattleboro

May 12 – 19

G$27,869 GYD per night
Guest favorite

Home in Spofford

5.0 out of 5 average rating, 8 reviews

A-Frame Cottage at Lake Spofford

Oct 1 – 8

G$49,136 GYD per night
Guest favorite

Home in Orange

4.95 out of 5 average rating, 21 reviews

The Zen Waterfront Retreat: A Sweetwater Stay

Jun 11 – 18

G$45,488 GYD per night
Guest favorite

Home in Orange

4.94 out of 5 average rating, 49 reviews

Four Season Cozy Lake House

Sep 2 – 9

G$47,748 GYD per night
Guest favorite

Home in Rindge

5.0 out of 5 average rating, 80 reviews

Waterfront escape

Sep 8 – 15

G$80,318 GYD per night
Guest favorite

Home in Rindge

4.9 out of 5 average rating, 21 reviews

Magic Lakehouse, Waterfront, Private Beach & Dock

Sep 26 – Oct 3

G$116,162 GYD per night
Guest favorite

Home in Belchertown

5.0 out of 5 average rating, 16 reviews

Moonstone n' Lucy's Lake House – romantic, serene

Mar 21 – 28

G$31,828 GYD per night
Guest favorite

Home in Ashburnham

4.92 out of 5 average rating, 36 reviews

Lake House with Island and boats!

Mar 1 – 8

G$49,630 GYD per night
Guest favorite

Home in Shutesbury

4.95 out of 5 average rating, 19 reviews

Lakeside 2 Bedroom House

Dec 13 – 20

G$50,992 GYD per night
Guest favorite

Home in Orange

4.9 out of 5 average rating, 67 reviews

Mike's Lake House

Apr 22 – 29

G$43,234 GYD per night
Guest favorite

Home in Alstead

5.0 out of 5 average rating, 17 reviews

The Lake House

May 25 – Jun 1

G$48,401 GYD per night

Other great vacation rentals in Winchester

Superhost

Cabin in Brattleboro

4.89 out of 5 average rating, 441 reviews

Cottage

Aug 14 – 21

G$27,571 GYD per night
Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 128 reviews

The Lake Cottage: A Sweetwater Stay

Oct 9 – 16

G$25,735 GYD per night
Guest favorite

Home in Chesterfield

4.97 out of 5 average rating, 225 reviews

Charming Country Home

Mar 9 – 16

G$36,526 GYD per night
Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 146 reviews

Cider House Cottage

Nov 6 – 13

G$29,016 GYD per night
Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 260 reviews

The Studio With a View. Bring your dog, too!

Oct 16 – 23

G$29,379 GYD per night
Guest favorite

Apartment in Brattleboro

4.89 out of 5 average rating, 313 reviews

Quiet St in Town, gardens, terrace

Apr 26 – May 3

G$25,006 GYD per night
Guest favorite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 197 reviews

Light Filled Loft in the Vermont Countryside

Apr 20 – 27

G$24,282 GYD per night
Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 220 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Sep 5 – 12

G$30,594 GYD per night
Guest favorite

Tiny home in Brattleboro

4.95 out of 5 average rating, 173 reviews

"Mountain View" Hike In Cabin Retreat

Aug 24 – 31

G$19,031 GYD per night
Guest favorite

Barn in Chester

4.99 out of 5 average rating, 487 reviews

Inviting studio apartment above barn in Vermont

Apr 24 – May 1

G$19,543 GYD per night
Superhost

Guesthouse in Fitzwilliam

4.86 out of 5 average rating, 331 reviews

Tranquil Guest House with Sauna

Dec 29 – Jan 5

G$30,553 GYD per night
Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 476 reviews

Serenity Now - Couples Retreat or Writer's Dream

Oct 25 – Nov 1

G$40,028 GYD per night

Destinations to explore