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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (25)
"Wonderful place it’s are 3rd time staying there an you can’t beat the location, pond view or the nature surrounding you. An a very fast response. I will be staying agsin!"
The price is $189
$407 total
includes taxes & fees
Jun 11 - Jun 12
Charming Waterfront Log Cabin
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
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Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (40)
"It was very welcoming and comfortable! Highly recommend!"
Spectacular Mountain views with all the amentities nearby
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (35)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Fridge, microwave, oven, stovetop
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
6.0 out of 10, (8)
"We loved staying in the Newfane home! I was a bit worried at 1st from reading the reviews but it was great. The house was nice and cozy. The sauna and steam tub were AMAZING. We really enjoyed the quiet and we were so close to such great restaurants. We would love to come back!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
Property grounds
Quiet private pond getaway
9.6 out of 10, Exceptional, (4)
"Needed a long weekend getaway. Perfect spot located in nature, great fishing and fall foliage."
Quiet private pond getaway
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is $211
$355 total
includes taxes & fees
May 29 - May 30
Family Friendly Hilltop House In Putney Vermont
Property grounds
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, (34)
"Stayed here to celebrate a birthday, hang out with friends, and go to Stratton. The house was amazing. We really enjoyed the record player and relaxing by the wood stove. The property was kept nicely and the home was very clean. The house had all of the standard things that are typically needed. We look forward to staying there again next year."
Cozy cottage tucked away in the woods
Exterior
Private Suite with a Sweet View. Spacious, close to town, dog friendly
10.0 out of 10, Exceptional, (24)
"A weekend getaway w a lifelong friend. We greatly enjoyed the beautiful view, sitting by the big windows in the morning, sipping coffee and catching up. It’s just what we needed. Shelburne Falls has a very nice Main Street (Bridge Street). The Blue Rock restaurant is a high recommend."
Private Suite with a Sweet View. Spacious, close to town, dog friendly
Property grounds
Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (4)
"We had a work get together and it is was perfect. There was a nice spot outside to socialize, and all of the sleeping areas were very comfy. Great stay."
The price is $185
$353 total
includes taxes & fees
May 27 - May 28
Downtown Hot Tub Escape
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (38)
"The house was very clean and cozy. Nice and peaceful get away in a remote cabin with my wife and both of the dogs! They provided dog toys and a bed for our pups with additional treats, they were very happy about this! If you are looking for a quiet get away to slow down and reconnect with your family this is the place to be!"
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Exterior
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, (54)
"Great location for our destination wedding nearby. Spacious home with a nice sunroom. Loved how you felt away from it all yet were very close to groceries, shops and restaurants."
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Property grounds
Charming Cottage by the Lake
Charming Cottage by the Lake
DVD player, books
Hilltop Home with Great Views
9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
Property grounds
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (58)
"We stayed as part of a business trip. Three floors each with a bathroom was the selling point for our team. Everything was clean and as described. We would stay again!"
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Don't see what you're looking for?
See all available properties in Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Winchester you may be interested in

Interior
The Colonial Hotel
3.0 star property
8.6 out of 10, Excellent, (832)
"We had a pleasant stay at The Colonial. It was relatively close to Game On in Fitchburg, where my daughter had a basketball tournament. It is a outdated, but very clean. The only negatives were they provided our room with minuscule size bottles of shampoo and conditioner, so we had to ask for more. Also, front desk was calling our phone around checkout to make sure we were out of the room. It made us feel they were rushing us out."
The price is $160
$175 total
includes taxes & fees
May 27 - May 28
The Colonial Hotel
Exterior
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, (1001)
"Great pool and hot tub facilities with kickers"
The price is $98
$108 total
includes taxes & fees
May 26 - May 27
Colonial Motel And Spa
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very Good, (1002)
"The room was quiet and clean. The staff was friendly. I would stay there again. "
The price is $75
$84 total
includes taxes & fees
May 28 - May 29
The Covered Bridge Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $185 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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 vacation rental in Winchester?

Yes, we give you a choice of vacation rentals in Winchester close to Rhododendron State Park, or you can select a secluded option if you'd like a relaxing place to 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's the top vacation rental that Winchester has to offer?

Charming Waterfront Log Cabin: This vacation home rental outside of Winchester is located on the waterfront and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Winchester?

Expedia has 3 vacation rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Birch Point and Pisgah State Park are a couple of lovely local spots to get outside and enjoy nature. While here, Rhododendron State Park and Ashuelot River are other places worth a visit.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a long or short time in Winchester. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.

Recent reviews of Winchester properties
Expedia verified reviews

The Putney Inn

The Putney Inn

5/5 Excellent
"Easy, quick check in, friendly staff. Some noise from neighbors to be expected. Very clean, good sleep, pleasant stay. Would return. "
A verified traveler stayed at The Putney Inn
Posted 4 days ago
The Putney Inn