Winchester Holiday Rentals from NZ$145: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winchester holiday rentals

A lakeside park with picnic tables and a concrete walkway.

1. 2 private mountain RV pads for rent. Full hook ups

Winchester

includes taxes & fees

11 Oct - 12 Oct

A rustic cabin with a covered porch, a small shed, and outdoor seating.

2. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Hinsdale

Adrienne

includes taxes & fees

25 Oct - 26 Oct

A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

3. Cozy Vermont Tiny Home Get Away

Brattleboro

includes taxes & fees

31 Oct - 1 Nov

A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

4. Yurt Oasis in the woods of Hinsdale, NH

Hinsdale

Troy H.

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

5. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

Fitzwilliam

Marie M.

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with a wooden countertop, dark cabinets, and a large window.

6. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

cody s.

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with granite countertops, stainless steel appliances, and a central island.

7. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Keene

Jeremy S.

includes taxes & fees

12 Oct - 13 Oct

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

8. Lovely 2nd Floor Apartment

Greenfield

Jane P.

includes taxes & fees

1 Nov - 2 Nov

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Winchester Hotel Reviews

Hampton Inn Brattleboro

8/10 Good

"Nice property. Room was nice and clean and Robert at the front desk was great."

Latchis Hotel

8/10 Good

"Love the old-fashioned, art, deco, charm, and having the turntables and old records in the room… And having the movie theater attached…. I think this is a work in progress. The carpeting is really old in the rooms and there were laundry bags left out for the laundry to pick up all day… And because they don’t staff from 10 PM to 9 AM on a Saturday I had to literally fill the water jug for the Keurig coffee from my tub… Could you not. But the staff was great and it’s a cool looking old hotel… The windows need to be clean so I could actually see the mountains out of my room… And be able to close the outside windows. If you want old World charm give it a try… But I’m hoping or not for private he has taken this over. I’ll put some more cash into it because it’s worth it."

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"We had a one night stay recently. We were on the newly-renovated 4th floor, which was very nice. The room was very clean. We were there early, so we went to the 99 Restaurants bar that was right in front of the Comfort Inn. Check-in was easy and the staff were very pleasant. Room was very nice. We did have an issue with the television, but staff responded quickly and solved the issue. The free breakfast in the morning was very nice. Pancakes, waffles (with fruit toppings & syrup), bacon, breads, bagels and muffins, fresh fruit, cereals, yogurts. Many beverage options. A very nice selection! Staff was right there to replenish anything that was running low. Parking was plentiful, and right in front of the entrance. Check-out was fast and easy. I would highly recommend Comfort Inn & Suites!"

Find out more about Winchester

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester. Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Rhododendron State Park, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Winchester. Make sure you have time to check out the forests and waterfront during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

Birch Point and Cass Pond are a couple of lovely local spots to get outside and enjoy nature. While here, Winchester Speedpark and New England Sweetwater Farm & Distillery are other places worth a visit.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester holiday rentals

1. 2 private mountain RV pads for rent. Full hook ups

2. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

3. Cozy Vermont Tiny Home Get Away

4. Yurt Oasis in the woods of Hinsdale, NH

5. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

6. Modern Downtown Escape HotTub Fire Pit Games 12ppl

7. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

8. Lovely 2nd Floor Apartment

9. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

10. Vikings Villages Resort - Double Bed Room

11. Family Friendly Hilltop House In Putney Vermont

12. Wellness Getaway with a Personal Sauna, and Private River Beach!

13. 2 Twin beds on 1st floor with En-suite bathroom.

14. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

15. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

16. Light-filled treetop apartment close to downtown Greenfield and Highland Park

17. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

18. The Studio with a View. Bring your dog, too!

19. Private bed with En-suite bathroom Marigold Room

20. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

Hampton Inn Brattleboro

Gardner Inn

The Colonial Hotel

Latchis Hotel

Otherland Hotel

Colonial Motel

The Inn At Crumpin Fox

Hampton Inn & Suites Greenfield

Comfort Inn & Suites Brattleboro I-91

Find out more about Winchester

Frequently asked questions

Go further with the Expedia app