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Winchester Holiday Rentals

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Holiday Rentals in Winchester

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

10.0 out of 10, Exceptional, (3)
"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!"
The price is NZ$436
includes taxes & fees
8 Sept - 9 Sept
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

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!

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (25)
"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, (16)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is NZ$821
includes taxes & fees
19 Aug - 20 Aug
Downtown Hot Tub Escape

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is NZ$304
includes taxes & fees
19 Aug - 20 Aug
Lovely 2nd Floor Apartment

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

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

8.6 out of 10, Excellent, (55)
"really enjoyed our stay. Place would be much better if there was a microwave."
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, (106)
"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, (21)
"Property was clean and super close to the downtown square! "
The price is NZ$320
includes taxes & fees
26 Aug - 27 Aug
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

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

10.0 out of 10, Exceptional, (55)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (22)
"Very pleasant stay."
Riverfront 2 Bedroom Unit 2

Quiet private pond getaway

9.4 out of 10, Exceptional, (13)
"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, (33)
"Was in town for a race with friends. Great base camp for before and after on an amazing property "
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 NZ$368
includes taxes & fees
9 Sept - 10 Sept
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (40)
"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)
"A dream Vt. property, peaceful and scenic, with no worries"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is NZ$484
includes taxes & fees
6 Sept - 7 Sept
Family Friendly Hilltop House In Putney Vermont

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (4)
"Beautiful cottage on the lake. Everything seams new and spotless. Would definitely stay again."
Modern Waterfront Gem w/ Dock on Lake Monomonac

Cozy cottage tucked away in the woods

9.8 out of 10, Exceptional, (44)
"Nice and comfy - loved the decor and the property."
Cozy cottage tucked away in the woods

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

9.8 out of 10, Exceptional, (51)
"Ryan’s property is beautiful and peaceful. Its exactly what I would describe as a perfect summer getaway."
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
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.