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Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

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, (38 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is NZ$369
includes taxes & fees
8 July - 9 July
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Cozy Campfire Camper Retreat - Lake Nearby!

Cozy Campfire Camper Retreat - Lake Nearby!
Henniker
The price is NZ$189
includes taxes & fees
27 June - 28 June
Cozy Campfire Camper Retreat - Lake Nearby!

HotTub FirePit Games Huge Backyard Family Friendly

HotTub FirePit Games Huge Backyard Family Friendly
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"We wanted a place where we could eat and spend time together while still having space for everyone else to stretch out and this hit all the right buttons. Family weekend to visit our grandson, a student at nearby NEC, After a 3 hour drive up from the Cape, followed by an afternoon at the mall and restocking his dorm room, the hot tub was just what the doctor ordered!Rebecca is a wonderful host, very responsive, friendly, and helpful!"
United States
Jean C.
The price is NZ$460
includes taxes & fees
30 June - 1 July
HotTub FirePit Games Huge Backyard Family Friendly

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
8.4 out of 10, Very good, (12 reviews)
"Host was communicative and helpful with some specific questions we had. The apartment was in a cute older house, nicely updated and set up for guests. Everything was nicely labeled to be easy to find. The hot tub was great as well!"
United States
Sarah H.
The price is NZ$478
includes taxes & fees
30 June - 1 July
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (4 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.
The price is NZ$832
includes taxes & fees
30 June - 1 July
Lakefront Family Fun Retreat

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (26 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is NZ$629
includes taxes & fees
24 June - 25 June
Modern Downtown Escape HotTub Fire Pit Games 12ppl

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Host was extremely welcoming and the place was great."
United States
Chad C.
The price is NZ$652
includes taxes & fees
25 June - 26 June
•   Blaisdel Serenity Retreat Minutes to Lake & Sunapee Area

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is NZ$550
includes taxes & fees
24 June - 25 June
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9 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
The price is NZ$500
includes taxes & fees
25 June - 26 June
Brook Road Cabin

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
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.
The price is NZ$913
includes taxes & fees
8 July - 9 July
Chic Farmhouse Decor | Deck w/View

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is NZ$849
includes taxes & fees
24 June - 25 June
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
9.8 out of 10, Exceptional, (10 reviews)
"This was a great property. We had a wonderful stay here for a large group. Rebecca is a great host- so responsive and helpful before and during our stay. Highly recommend! "
United States
Kyra D.
The price is NZ$1,207
includes taxes & fees
30 June - 1 July
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (25 reviews)
"We stayed again because the first visit was so perfect! Beautiful, peaceful house in a gorgeous setting. Wonderful hosts!"
United States
Amanda R.
The price is NZ$946
includes taxes & fees
29 June - 30 June
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

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.
The price is NZ$492
includes taxes & fees
24 June - 25 June
Room 10 - Queen Room

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Bennington
10.0 out of 10, Exceptional, (13 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is NZ$681
includes taxes & fees
15 July - 16 July
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking

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, (30 reviews)
"The Treehouse provided an excellent retreat. Beautiful property and excellent hosts. "
United States
T G.
The price is NZ$846
includes taxes & fees
24 June - 25 June
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee

Boutique Cottage Near Lake Sunapee | Fire Pit + View

Boutique Cottage Near Lake Sunapee | Fire Pit + View
New London
10.0 out of 10, Exceptional, (105 reviews)
"Lovely home. Very clean and nicely renovated. Will stay again when back in the area!"
United States
Cheryl S.
The price is NZ$1,112
includes taxes & fees
24 June - 25 June
Boutique Cottage Near Lake Sunapee | Fire Pit + View

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
New London
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic property and host! An excellent home base for skiing at Mt. Sunapee. Especially loved the hot tub and fire pit."
United States
Kurt W.
The price is NZ$2,454
includes taxes & fees
24 June - 25 June
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

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, (21 reviews)
"Beautiful house and convenient location for a family ski trip. We'lll be back in the summer! "
United States
Rebecca B.
The price is NZ$1,235
includes taxes & fees
15 July - 16 July
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

“Big Red” @ New London/Sunapee - Overflow Unit

“Big Red” @ New London/Sunapee - Overflow Unit
New London
The price is NZ$2,793
includes taxes & fees
24 June - 25 June
“Big Red” @ New London/Sunapee - Overflow Unit
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

Find out more about Windsor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!: This holiday home rental outside of Windsor is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Windsor?

Expedia has 5 holiday rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Eaton's Magic Morsel, or get out into nature at a spot like Black Pond. In the wider area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.