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Winchester Holiday Rentals

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Holiday Rentals in Winchester

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is AU$312
includes taxes & fees
14 Aug - 15 Aug
Lovely 2nd Floor Apartment

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (24)
"Very nice, clean, and great area. We enjoyed it very much!"
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is AU$746
includes taxes & fees
11 Aug - 12 Aug
Downtown Hot Tub Escape

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (27)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (12)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

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

10.0 out of 10, Exceptional, (5)
"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! :)"
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

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

10.0 out of 10, Exceptional, (53)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

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

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (105)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

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

9.8 out of 10, Exceptional, (20)
"Property was clean and super close to the downtown square! "
The price is AU$293
includes taxes & fees
12 Aug - 13 Aug
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

10.0 out of 10, Exceptional, (1)
"This was the definition of a New England inn!! Super cute and the staff were fantastic! They were so helpful! I would definitely stay here again!! "
The price is AU$320
includes taxes & fees
21 Aug - 22 Aug
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (43)
"Nice and comfy - loved the decor and the property."
Cozy cottage tucked away in the woods

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (81)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (21)
"Very pleasant stay."
Riverfront 2 Bedroom Unit 2

Quiet private pond getaway

9.4 out of 10, Exceptional, (11)
"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!"
Quiet private pond getaway

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (32)
"The cabin was great, beautiful surroundings. Very nice house."
Jacksonville Cabin w/ Wraparound Deck & Views

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"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!"
The price is AU$349
includes taxes & fees
7 Sept - 8 Sept
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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

8.4 out of 10, Very good, (29)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (39)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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

10.0 out of 10, Exceptional, (45)
"Our stay at Fiddlers Rest was PERFECT! It was a great cozy getaway for our family and dog. The accommodations were excellent and the host did a wonderful job providing everything that was needed for a wonderful weekend getaway. We definitely will be coming back! "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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.
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Top Winchester Hotel Reviews

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?

Lovely 2nd Floor Apartment: This holiday home rental outside of Winchester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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?

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.