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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Windsor vacation rentals

A compact kitchen with modern appliances, a wooden dining table, and a view through a window.

1. Family Friendly, Hot Tub, King Beds Just Renovated

Family Friendly, Hot Tub, King Beds Just Renovated
Hillsborough
$316 nightly
The price is $343
Oct 14 - Oct 15
Total with taxes and fees
Family Friendly, Hot Tub, King Beds Just Renovated
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

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

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (47 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
$194 nightly
The price is $210
Nov 9 - Nov 10
Total with taxes and fees
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A stone fireplace with a clock above it, a television mounted on the wall, and a wooden door.

3. •   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (23 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
$352 nightly
The price is $381
Oct 19 - Oct 20
Total with taxes and fees
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

4. SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!

SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
Newbury
9.8 out of 10, Exceptional, (21 reviews)
"Neat place, close to two ski mountains. "
United States
COLLEEN K.
$1,039 nightly
The price is $1,127
Oct 20 - Oct 21
Total with taxes and fees
SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

5. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
$381 nightly
The price is $413
Nov 2 - Nov 3
Total with taxes and fees
Lakefront Family Fun Retreat
A conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

6. Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
Bennington
10.0 out of 10, Exceptional, (16 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
$367 nightly
The price is $398
Oct 18 - Oct 19
Total with taxes and fees
Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

7. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
$583 nightly
The price is $632
Oct 14 - Oct 15
Total with taxes and fees
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A cozy living room with a large sectional sofa, a wooden coffee table, and a view of trees through a window.

8. Brook Road Cabin

Brook Road Cabin
Goshen
9.6 out of 10, Exceptional, (18 reviews)
"Would go back!"
United States
Elizabeth C.
$298 nightly
The price is $323
Oct 15 - Oct 16
Total with taxes and fees
Brook Road Cabin
A modern living room with a flat-screen TV, a sectional sofa, a coffee table, and a large window providing a view of the outdoors.

9. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
10.0 out of 10, Exceptional, (11 reviews)
"Great place to relax with a woody vibe. Excellent stay"
United States
Logan V.
$625 nightly
The price is $678
Oct 18 - Oct 19
Total with taxes and fees
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

10. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
$282 nightly
The price is $306
Oct 15 - Oct 16
Total with taxes and fees
Brook Road Cabin
A cluster of white buildings with multiple chimneys, surrounded by lush green grass and trees with autumn foliage.

11. Room 10 - Queen Room

Room 10 - Queen Room
Francestown
10.0 out of 10, Exceptional, (1 review)
"Easy access to skiing Crotched mountain, great breakfast and dinner! Lovely people!"
United States
j l.
$265 nightly
The price is $288
Nov 3 - Nov 4
Total with taxes and fees
Room 10 - Queen Room
A yellow building with a porch and a sign that reads "Brook Road Inn."

12. Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Nice place for a mountain stay"
United States
Meghan B.
$296 nightly
The price is $321
Oct 19 - Oct 20
Total with taxes and fees
Brook Road Condo
A wooden cabin with a balcony, surrounded by trees.

13. Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.6 out of 10, Exceptional, (27 reviews)
"Amazing weekend stay with our pup! Looking forward to staying here in the summer! "
United States
Naydene G.
$398 nightly
The price is $432
Oct 15 - Oct 16
Total with taxes and fees
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
A wooden cabin with multiple windows and a balcony, surrounded by trees.

14. Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (32 reviews)
"The Treehouse provided an excellent retreat. Beautiful property and excellent hosts. "
United States
T G.
$451 nightly
The price is $489
Oct 28 - Oct 29
Total with taxes and fees
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

15. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
$393 nightly
The price is $427
Oct 14 - Oct 15
Total with taxes and fees
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

16. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
$294 nightly
The price is $315
Nov 1 - Nov 2
Total with taxes and fees
Cozy Tiny House on Main Street. Fully Renovated.
A wooden interior with a dining table and chairs, a kitchen area, and large windows.

17. Spectacular Fall Color! 20 Min to Ragged Mtn and Mt. Sunapee | Sleeps 6

Spectacular Fall Color! 20 Min to Ragged Mtn and Mt. Sunapee | Sleeps 6
North Sutton
$591 nightly
The price is $641
Nov 3 - Nov 4
Total with taxes and fees
Spectacular Fall Color! 20 Min to Ragged Mtn and Mt. Sunapee | Sleeps 6
A two-story house with a front porch, a staircase, and a small garden area.

18. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (9 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
$155 nightly
The price is $168
Oct 19 - Oct 20
Total with taxes and fees
Central Large 2-bedrooms with office in Keene
A forested area with a gravel path leading to a cabin with a metal roof and a wooden deck.

19. Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (28 reviews)
"The place was clean and very comfortable"
United States
Pam D.
$450 nightly
The price is $488
Oct 14 - Oct 15
Total with taxes and fees
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

20. Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
$276 nightly
The price is $299
Oct 19 - Oct 20
Total with taxes and fees
Brook Road Condo
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 Windsor Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"I got a quiet room to stay. That was great. Staff was very nice and helpful. Cleaners came every day to clean room"
Vandana 3-night trip
Posted 14 hours ago
Days Inn by Wyndham Keene NH

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $210 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, you can find vacation rentals near well known attractions in Windsor, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental in Windsor?

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.: This vacation home near Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a library.

How many vacation rentals will I find in Windsor?

Expedia has 5 vacation rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Friendly Farm, or get out into nature at a spot like Black Pond. In the larger area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a vacation rental in Windsor like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Windsor. Vacation rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for small groups.