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Winchester Holiday Rentals

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Check prices for these dates

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

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

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

10.0 out of 10, Exceptional, (4)
"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!"
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Riverside Retreat – Cozy 2-Story Getaway!
Fridge, microwave, oven, stovetop

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (28)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (26)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (34)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is HK$907
HK$1,589 total
includes taxes & fees
28 Aug - 29 Aug
Lovely 2nd Floor Apartment
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is HK$2,093
HK$3,517 total
includes taxes & fees
2 Sept - 3 Sept
Downtown Hot Tub Escape
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

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
Outdoor dining

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

8.6 out of 10, Excellent, (56)
"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
Jacksonville Cabin w/ Wraparound Deck & Views
Dining

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
Quiet private pond getaway
Property grounds

Quiet private pond getaway

9.4 out of 10, Exceptional, (14)
"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
Beautiful Custom Built Timber Frame Home, Sleeps 11
Smart TV, fireplace, DVD player, ping pong

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
Family Friendly Hilltop House In Putney Vermont
Property grounds

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 HK$1,523
HK$2,669 total
includes taxes & fees
13 Sept - 14 Sept
Family Friendly Hilltop House In Putney Vermont
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Exterior

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

10.0 out of 10, Exceptional, (67)
"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."
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (57)
"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
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (22)
"Property was clean and super close to the downtown square! "
The price is HK$809
HK$1,471 total
includes taxes & fees
8 Sept - 9 Sept
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Riverfront 2 Bedroom Unit 2
Microwave, oven, stovetop

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (23)
"Very pleasant stay."
Riverfront 2 Bedroom Unit 2
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker

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

10.0 out of 10, Exceptional, (46)
"A dream Vt. property, peaceful and scenic, with no worries"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Wellness Getaway with a Personal Sauna, and Private River Beach!
Sauna

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
The price is HK$1,055
HK$1,995 total
includes taxes & fees
8 Sept - 9 Sept
Wellness Getaway with a Personal Sauna, and Private River Beach!
Charming Waterfront Log Cabin
3 bedrooms, travel cot, free WiFi, bed sheets

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

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

9.2 out of 10, Wonderful, (17)
"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"Loved the area"
The price is HK$1,062
HK$1,729 total
includes taxes & fees
9 Sept - 10 Sept
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
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

Blooming Inn

Blooming Inn

10/10 Excellent
"T"
Marcela 1-night trip
Posted 9 hours ago
Blooming Inn

Find out more about Winchester

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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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.

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, Pisgah State Park and New England Sweetwater Farm & Distillery 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.