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Top Holiday Rentals in Winchester

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (19)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (52)
"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."
The Jelly Mill-A Peaceful River Retreat

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (17)
"This place was perfect for our stay! It was clean, nicely decorated/designed and had thoughtful touches. The pictures were spot on for what to expect, it was peaceful, and the view was lovely. Crystal was great and check-in/out was easy! We would definitely stay here again."
Lakefront Orange Vacation Rental - Pet Friendly!

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

9.8 out of 10, Exceptional, (18)
"Property was clean and super close to the downtown square! "
The price is £137
includes taxes & fees
8 Jul - 9 Jul
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (135)
"A terrific, cozy place, convenient, in a cute neighborhood -- super easy check in --- clear directions --- couldn't ask for anything more."
Beautiful Townhouse In Turners Falls!

Downtown Hot Tub Escape

9.2 out of 10, Wonderful, (14)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is £346
includes taxes & fees
29 Jun - 30 Jun
Downtown Hot Tub Escape

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (38)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (26)
"Easy stay, good location for us. Would stay again. "
The price is £136
includes taxes & fees
2 Jul - 3 Jul
Lovely 2nd Floor Apartment

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

8.8 out of 10, Excellent, (47)
"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

Quiet private pond getaway

9.4 out of 10, Exceptional, (9)
"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

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

10.0 out of 10, Exceptional, (52)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

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

10.0 out of 10, Exceptional, (77)
"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

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (2)
"We stayed here for couple of days. We loved it all! The place is lovely, very clean, spacious, big, and very convenient. The price is very reasonable. The property is beautiful overall! It has orchard trees and a lake. It reminded us the Vermont house in the movie Baby Boom. The location is very convenient too. 10 mins of driving to the MT Snow Ski Resort with lots of winter activities , and also 10 mins of driving to town center of West Dover. We walked in town and shopped in the small...
The price is £154
includes taxes & fees
30 Jun - 1 Jul
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

2.0 star property
9.0 out of 10, Wonderful, (8)
"Needed place to stay in Ashburnham large enough to sleep extended family traveling in for the holidays. Cabin was quaint, rustic and fit all of us. Overall good stay. "
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

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 £160
includes taxes & fees
29 Jun - 30 Jun
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (55)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is £253
includes taxes & fees
29 Jun - 30 Jun
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

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!

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (54)
"Beautifully decorated retreat in the treetops."
Spectacular Mountain views with all the amentities nearby

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

8.4 out of 10, Very good, (28)
"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
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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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?

The Jelly Mill-A Peaceful River Retreat: This holiday home rental outside of Winchester is located on a river, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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?

Rhododendron State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, New England Sweetwater Farm & Distillery and Winchester Speedpark 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.