Winchester Holiday Rentals from €289: Search Short-Term Rentals

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Holiday Rentals in Winchester

"Great place to stay with friends and family. Will be visiting again!"

"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"

"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "

"My friends and I stayed a night while we went ice fishing out on the lake. The house was great, right on the lake, and James the host was awesome. Loved his vibe and the house had everything we needed. We ran out of time for the sauna but that's first on my list for next time. "

includes taxes & fees

24 Feb - 25 Feb

"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "

"Great host"

"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...

"Would recommend if anyone wants a quiet, peaceful getaway."

3 bedrooms, travel cot, free WiFi, bed sheets

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

Fridge, microwave, stovetop, coffee/tea maker

"Great little cabin, would definitely stay again!"

"We loved this cabin in the woods. This was our second stay here. More than enough room for my wife and I and 26 year old daughter. Beautiful and rustic with a working wood stove and plenty of wood on hand. Kitchen is well stocked. Be warned that road access is a little challenging - steep unpaved road to get there - but our non-4x4 minivan could make it. Lots of good hiking in nearby Jamaica, and the neighboring small towns are charming. Craig was a great host and very responsive."

"We had another great stay for us at the Fiddler's rest. The cabin is beautifully set in a private stetting in the forest. The interior design is colorful and tasteful. The cabin could comfortable host or group of 4 people. The internet connection was great. We would be happy to visit again!"

"We stayed three nights here. Just the two of us. I felt the pictures were misleading. Much smaller than expected. Since it was just the two of us it was perfect. "

"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."

"Small but very clean and had everything we needed for our stay "

Video games, DVD player, ping pong, books

"Great house for groups or a big family. Lots of games/arcade/ping pong. Hot tub jazuzzi tub in the master bedroom were so nice to have.It was an investment, but was worth it to be able to have the whole family comfortably. "

"The place and location are gorgeous, we absolutely loved it."

"Stunning property, we had the best time for our annual friendsgiving. The kids loved the backyard and the two kitchens was awesome! "

"This was our 2nd stay with the host. Everything was perfect and relaxing. "

includes taxes & fees

23 Feb - 24 Feb

"We rented the house for a weekend and it was spacious, clean, and comfortable. The kitchen and bathrooms are well stocked with essentials and the views are splendid. The owner was very easy to communicate with and incredibly responsive to any questions/needs."

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"All ok everything worked well just older decor "

includes taxes & fees

17 Feb - 18 Feb

"."

includes taxes & fees

23 Feb - 24 Feb

"Property is very nice but walls are thin and there is a gazebo for smoking, outdoor grilling, and shooting off fireworks that is located on the grounds of the hotel. Lots of noise, was tough to sleep."

includes taxes & fees

3 Mar - 4 Mar

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 €289 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.

Recent reviews of Winchester properties

5/5 Excellent

"One of the best places I stayed. Very beautiful place, great staff working there I was really impressed. Will be back!"

A verified traveller stayed at Hampton Inn & Suites Greenfield

Posted 2 days ago

5/5 Excellent

"Excellent place to stay. A short and beautiful drive to Mount snow. The folks running the place really go the extra mile. I was most amazed at not only the timely clearing of the parking lots well before 7 am from 6 inches of snow, but also at then clearing the snow of all the vehicles parked there! Will certainly be back to stay here again"

A verified traveller from Edison stayed at The Lodge at West River

Posted 2 days ago

5/5 Excellent

Great location and a comfortable stay

"We enjoy our stay and the convenience of the toaster (for our own bread) in the lobby and hot water (for our own drinks), that we are allowed to use. The hotel is generally clean but we did encounter trash next to the bed and also the hair dryer once time still plugged into the wall. There we would recommend to retrain the cleaning crew to ensure that everything is cleaned and cleaned out and that everything is put back in its place. "

A verified traveller stayed at The Putney Inn

Posted 3 days ago

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.

How many holiday rentals will I find in Winchester?

Expedia has 3 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Pisgah State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, Birch Point and Rhododendron 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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Check prices for these dates

Holiday Rentals in Winchester

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

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

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

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

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

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

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Spectacular Mountain views with all the amentities nearby

Spectacular Mountain views with all the amentities nearby

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Charming Waterfront Log Cabin

Charming Waterfront Log Cabin

Hike & Swim On-Site: Cozy Falls Brook Cabin

Hike & Swim On-Site: Cozy Falls Brook Cabin

Cozy cottage tucked away in the woods

Cozy cottage tucked away in the woods

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

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

Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table

The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Cozy 2-bedroom Unit with private backyard

Cozy 2-bedroom Unit with private backyard

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

Spectacular 4 Season Home on Spruce Lake

Spectacular 4 Season Home on Spruce Lake

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

Beautiful Modern Cottage with Sauna on Lake Monomonac

Beautiful Modern Cottage with Sauna on Lake Monomonac

Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking

Charming 4 bedroom house with Views, 200 acres, Private Schools, Ski, Hiking

Other types of properties in Winchester you may be interested in

Colonial Motel And Spa

Colonial Motel And Spa

The Colonial Hotel

The Colonial Hotel

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Find out more about Winchester

Find out more about Winchester

Recent reviews of Winchester properties

Recent reviews of Winchester properties

Hampton Inn & Suites Greenfield

Frequently asked questions