Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite

Cottage in Bernardston

4.88 out of 5 average rating, 285 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.

13–20 Dec

$242 NZD per night

Guest favourite

Apartment in Greenfield

4.96 out of 5 average rating, 267 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.

24–31 Jul

$198 NZD per night

Guest favourite

Apartment in Dublin

4.96 out of 5 average rating, 181 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.

28 Sep – 5 Oct

$212 NZD per night

Superhost

Guest suite in Montague

4.93 out of 5 average rating, 162 reviews

Great Falls Private Suite

Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the Connecticut River. Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon, 2 miles from downtown Turners Falls and 2.6 miles from downtown Greenfield. If you are looking for a private and bright suite with beautiful natural light and a modern bohemian feel this guest retreat is for you. I look forward to hosting you!

2–9 Jun

$187 NZD per night

Guest favourite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 426 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

18–25 Jun

$193 NZD per night

Guest favourite

Apartment in Winchester

4.93 out of 5 average rating, 160 reviews

Downtown Loft above Winery and Distillery

Enjoy a lovely weekend getaway in this cute 1 bedroom loft, centrally located in Winchester, NH. Enjoy a tasting at New England Sweetwater Farm & Distillery next door and a pint on us at Outlaw Brewing Company. This cozy loft features a full kitchen, 3/4 bath as well as a bedroom and living/dining room. 20 minutes to Keene, Brattleboro and Chesterfield. Access to Pisgah State Park, the Ahsuelot Rail Trail and Forest Lake. Come see what our beautiful area has to offer!

1–8 Nov

$169 NZD per night

Guest favourite

Guest suite in Brattleboro

4.94 out of 5 average rating, 517 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

4–11 Nov

$184 NZD per night

Guest favourite

Apartment in Brattleboro

4.96 out of 5 average rating, 148 reviews

Contemporary forest eco-retreat, mountain views

This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

1–8 May

$230 NZD per night

Guest favourite

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 124 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

24 Apr – 1 May

$178 NZD per night

Guest favourite

Cottage in Orange

4.95 out of 5 average rating, 196 reviews

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a newly designed vacation home with breathtaking views of Tully Mountain. This 4-season Cottage has real salvaged barn wood walls; up-cycled maple floors and one-of-a kind scratch built furniture and lighting fixtures. The deconstructed architecture leaves exposed the electrical conduit and copper plumbing pipes, making the cottage feel alive and organic.

30 Nov – 7 Dec

$318 NZD per night

Guest favourite

Apartment in Dummerston

4.96 out of 5 average rating, 158 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

26 Jun – 3 Jul

$175 NZD per night

Guest favourite

Apartment in Brattleboro

4.9 out of 5 average rating, 483 reviews

Cozy, Private & Great location for exploring VT !

The apartment is centrally located, cozy, quiet and private. It has been set up to be a comfortable retreat. It's private entrance leads upstairs to an open living room/ kitchen space. The back door opens to a deck overlooking a ball field and green hills. The sleeping nook contains a queen size , metal framed bed. The mattress is comfortable and the sheets are soft. VT charges 10% tax

4–11 Oct

$180 NZD per night