Winchester Holiday Rentals from €140: Search Short-Term Rentals

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

Downtown Hot Tub Escape : This holiday home rental outside of Winchester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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Holiday Rentals in Winchester

"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"

includes taxes & fees

2 Sept - 3 Sept

"Interior amazing. Exterior could use some attention"

"Very nice, clean, and great area. We enjoyed it very much!"

includes taxes & fees

25 Aug - 26 Aug

"Easy stay, good location for us. Would stay again. "

includes taxes & fees

27 Aug - 28 Aug

"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "

includes taxes & fees

25 Aug - 26 Aug

"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"

"really enjoyed our stay. Place would be much better if there was a microwave."

"Was in town for a race with friends. Great base camp for before and after on an amazing property "

"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"

Smart TV, fireplace, DVD player, ping pong

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

"We enjoyed our stay at this beautiful spacious property. The owner was very helpful and responsive. I’d definitely recommend staying here if you are in the area."

"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

includes taxes & fees

25 Aug - 26 Aug

"Property was clean and super close to the downtown square! "

includes taxes & fees

26 Aug - 27 Aug

"Very pleasant stay."

Fridge, microwave, stovetop, coffee/tea maker

"A dream Vt. property, peaceful and scenic, with no worries"

"The folks are SUPER and made me feel very welome"

includes taxes & fees

28 Aug - 29 Aug

3 bedrooms, travel cot, free WiFi, bed sheets

"We really appreciated the solitude and quiet retreat this cabin offered. "

"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"

"What an absolutely charming place!! It was so lovely staying here. This place is exactly what we wanted... a little weekend escape not too far from home, nestled in the woods. Absolutely beautiful. The hosts were so kind, too!"

includes taxes & fees

9 Sept - 10 Sept

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Top Winchester Hotel Reviews

Vikings Villages Resort

10/10 Excellent

"Our stay at Vikings Villages was fantastic. The cottages are done very tastefully, have everything you need and are very clean. The grounds are beautiful, there's a nice firepit to enjoy in the evening. We loved watching the sheep also. The owner was very friendly and helpful with restaurant suggestions. We'll definitely be back for a longer stay in the future. "

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Downtown Hot Tub Escape: This holiday home rental outside of Winchester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Winchester?

Richmond Wildlife Manangement Area and Rhododendron State Park are a couple of lovely local spots to get outside and enjoy nature. While here, New England Sweetwater Farm & Distillery and Pisgah State Park 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.

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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Riverside Retreat – Cozy 2-Story Getaway!

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Lovely 2nd Floor Apartment

Downtown Hot Tub Escape

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

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Jacksonville Cabin w/ Wraparound Deck & Views

Quiet private pond getaway

Beautiful Custom Built Timber Frame Home, Sleeps 11

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Family Friendly Hilltop House In Putney Vermont

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

Riverfront 2 Bedroom Unit 2

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

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

Charming Waterfront Log Cabin

Rustic, dog-friendly escape with private pool, sweeping views, & W/D

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Top Winchester Hotel Reviews

Vikings Villages Resort

Hampton Inn & Suites Greenfield

Hampton Inn Brattleboro

Keene Elm City Hotel, Ascend Hotel Collection

Comfort Inn & Suites Brattleboro I-91

Best Western Plus Keene Hotel

The Colonial Hotel

The Putney Inn

Colonial Motel And Spa

Find out more about Winchester

Frequently asked questions