Photo by Donny Campos

Search Vacation Homes in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 112 Vacation Homes in Winchester with updated reviews, rates, and availability.

Bright three-level home with water views, jetted tub, firepit, and pool table
Fridge, microwave, oven, stovetop

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

8.4 out of 10, Very Good, (27)
"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
Family Friendly Hilltop House In Putney Vermont
Exterior

Family Friendly Hilltop House In Putney Vermont

9.6 out of 10, Exceptional, (54)
"We were caught in the winter storm, and the host was so kind in helping us navigate our car situation. Our kids had such a great time playing in the snow, exploring the books and games they had. "
The price is AED 716
AED 1,230 total
includes taxes & fees
25 Mar - 26 Mar
Family Friendly Hilltop House In Putney Vermont
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Property grounds

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

10.0 out of 10, Exceptional, (71)
"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
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Fridge, microwave, oven, stovetop

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (15)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (7)
"We really enjoyed ourselves in Marcella's home, to the point where we did not want to leave the house to go skiing/snowboarding. Upon arrival you are greeted with a cute little bridge to cross over and you see a beautiful red house and barn. The home was very comfortable, with enough bedrooms and space for us our group to be in the kitchen or playing in the pool area, basketball court, ping pong table or 3 different sitting areas and hot tub. The kitchen has everything that you need from...
GAMERS HAVEN, River Wine Inn!
Lovely 2nd Floor Apartment
Fridge, microwave, oven, stovetop

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (19)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is AED 474
AED 792 total
includes taxes & fees
1 Apr - 2 Apr
Lovely 2nd Floor Apartment
Hilltop Home with Great Views
Interior

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
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (45)
"The Jelly Mill is a lovely, welcoming cottage in the S. VT town of Guilford, nestled in the hills below the bigger town of Brattleboro. The location feels 'out of the way' - no big roads (or even paved roads), stores, 'hustle or bustle' anywhere close by - but Brattleboro has all that stuff and is only 20-30 minutes away. For 'last minute' items a charming, smaller grocery / sandwich shop is closer by. The property itself is very clean, with an up to date kitchen and glitch-free speedy Wi-Fi...
The Jelly Mill-A River Retreat
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, (52)
"Overall, the property checked all of our boxes. Location, space for number of guests, amenities, etc. Kitchen was fully stocked.Plowing of the driveway was key with a snow/ice storm in the middle of our stay.Internet speed was also fast as well for a full house of connected teens.There are not quite enough full bathrooms/showers for the number of possible guests especially in the upstairs space.The main tv/apps were glitchy. That needs to be looked at and updated. The firestick in the main...
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
TV

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

9.4 out of 10, Exceptional, (15)
"We had a fun time enjoying the view and playing board games plus outdoor pursuits. Thanks for sharing your home."
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
Modern Waterfront Gem w/ Dock on Lake Monomonac
Fridge, coffee/tea maker, toaster, cookware/dishes/utensils

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (1)
""Our stay at the Lake Monomonac cottage was absolutely perfect! The home was impeccably clean, beautifully decorated, and had everything we needed for a comfortable stay. The location was ideal for us to visit family nearby. The host was incredibly responsive and accommodating. We will definitely book again!"
Modern Waterfront Gem w/ Dock on Lake Monomonac
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Fridge, microwave, oven, stovetop

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Beautiful, private log cabin with huge, relaxing screened porch
Outdoor dining

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (35)
"The property is exactly as stated in the listing. The host is extremely responsive and great at communicating. The beds were very comfortable and plenty of space for 6 adults. The kitchen was well stocked as well as the wood pile for the stove. Nothing but the best for the property and host. Thank you, Beth!"
Beautiful, private log cabin with huge, relaxing screened porch
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Property grounds

Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

9.8 out of 10, Exceptional, (25)
"We had an amazing week at the Tyler House. The house and location are among the best on the lake. The host lives nearby and is happy to assist with any requests."
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Mount Snow Post and Beam House
Fridge, oven, stovetop, dishwasher

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (38)
"Doug’s house is gorgeous and he was very communicative and helpful the entirety of our stay! Special thanks to Ryan for making sure we got out following a massive snow storm"
Mount Snow Post and Beam House
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,102
AED 1,909 total
includes taxes & fees
3 Apr - 4 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
River House
Outdoor dining

River House

2.0 star property
10.0 out of 10, Exceptional, (8)
"Me and a few friends stayed at the River House during a long weekend during the Winter. The house itself was very nice and had many amenities.The location is good for some of the ski resorts in lower Vermont. However there was a rather large snow storm and due to the half hour 40 minute drive to the mountain we were not able to go because of the roads. This was no fault of the owners obviously but if you want to guarantee getting to the mountain maybe pick a place closer and have access to a car...
River House
Nestled on the edge of the woods near Mount Monadnock
Fridge, microwave, oven, stovetop

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"House is comfortable and well stocked."
Nestled on the edge of the woods near Mount Monadnock
Peaceful 3-BR Cabin 40-Min to Stratton
Fridge, microwave, oven, stovetop

Peaceful 3-BR Cabin 40-Min to Stratton

2.0 star property
10.0 out of 10, Exceptional, (5)
"A beautiful cabin with all the amenities to relaxThank you "
Peaceful 3-BR Cabin 40-Min to Stratton
The Dover Hideaway | Hot Tub & Close to Mt. Snow
Fridge, microwave, oven, stovetop

The Dover Hideaway | Hot Tub & Close to Mt. Snow

The Dover Hideaway | Hot Tub & Close to Mt. Snow
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,102
AED 1,909 total
includes taxes & fees
3 Apr - 4 Apr
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (45)
"The Jelly Mill is a lovely, welcoming cottage in the S. VT town of Guilford, nestled in the hills below the bigger town of Brattleboro. The location feels 'out of the way' - no big roads (or even paved roads), stores, 'hustle or bustle' anywhere close by - but Brattleboro has all that stuff and is only 20-30 minutes away. For 'last minute' items a charming, smaller grocery / sandwich shop is closer by. The property itself is very clean, with an up to date kitchen and glitch-free speedy Wi-Fi...
The Jelly Mill-A River Retreat
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.8 out of 10, Exceptional, (16)
"We had a lovely time in central Mass"
Riverfront 2 Bedroom Unit 2
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.