Windsor Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Windsor holiday rentals

Beach towels

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 HK$1,245
HK$2,158 total
includes taxes & fees
8 Jun - 9 Jun
HotTub FirePit Games Huge Backyard Family Friendly
Interior

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"everything was perfect "
United States
Stephen C.
The price is HK$1,480
HK$3,254 total
includes taxes & fees
16 May - 17 May
Chic Farmhouse Decor | Deck w/View
Exterior detail

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, (35 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is HK$599
HK$1,245 total
includes taxes & fees
20 May - 21 May
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Terrace/patio

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
8.4 out of 10, Very good, (11 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 HK$1,120
HK$2,074 total
includes taxes & fees
18 May - 19 May
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Interior

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, (20 reviews)
"Our host went above and beyond to make our experience memorable. The house was very clean and we had a nice bottle of wine and snacks waiting for us. This house is close to the mountain and right near the lake. We will rent here again "
United States
Walter B.
The price is HK$1,480
HK$3,534 total
includes taxes & fees
17 May - 18 May
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
The price is HK$1,331
HK$2,506 total
includes taxes & fees
17 May - 18 May
Brook Road Condo
Interior

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, (12 reviews)
"The house was super clean, great distance to the mountain for skiing and restaurants, and the host was extremely helpful and accommodating!"
United States
Stephen S.
The price is HK$1,127
HK$2,532 total
includes taxes & fees
26 May - 27 May
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Interior

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Greenfield
10.0 out of 10, Exceptional, (15 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
The price is HK$1,449
HK$2,064 total
includes taxes & fees
28 May - 29 May
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Interior

Modern Chalet by Mt. Sunapee with Spa

Modern Chalet by Mt. Sunapee with Spa
Goshen
The price is HK$3,054
HK$5,242 total
includes taxes & fees
26 May - 27 May
Modern Chalet by Mt. Sunapee with Spa
Living room

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 HK$1,438
HK$2,341 total
includes taxes & fees
17 May - 18 May
Brook Road Cabin
TV

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 HK$1,331
HK$2,396 total
includes taxes & fees
17 May - 18 May
Brook Road Cabin
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"Amazing property! Would definitely stay here again "
New Zealand
Jackie M.
The price is HK$1,889
HK$3,510 total
includes taxes & fees
17 May - 18 May
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is HK$2,153
HK$2,659 total
includes taxes & fees
17 May - 18 May
Owl's Nest Treehouse
Interior

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

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 HK$1,628
HK$2,013 total
includes taxes & fees
17 May - 18 May
Room 10 - Queen Room
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is HK$1,298
HK$2,572 total
includes taxes & fees
20 May - 21 May
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Outdoor pool

Ski Minutes Away & Pool Onsite

Ski Minutes Away & Pool Onsite
Henniker
10.0 out of 10, Exceptional, (10 reviews)
"A lovely place to stay while visiting the area for the weekend. Key pad check in was seamless, and communication with the host was top notch. Would recommend and stay here again!"
United States
Sarah A.
The price is HK$1,261
HK$3,314 total
includes taxes & fees
18 May - 19 May
Ski Minutes Away & Pool Onsite
Fridge, microwave, oven, stovetop

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 HK$1,762
HK$4,341 total
includes taxes & fees
18 May - 19 May
Boutique Cottage Near Lake Sunapee | Fire Pit + View
Terrace/patio

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, (9 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 HK$1,832
HK$3,679 total
includes taxes & fees
20 May - 21 May
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
In-room dining

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
The price is HK$1,441
HK$2,345 total
includes taxes & fees
17 May - 18 May
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Clean rooms, the full breakfast was a great addition! Friendly staff, clean pool!!!"
Tracie 6-night trip
Posted 3 hours ago
Best Western Plus Keene Hotel

Find out more about Windsor

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

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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

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?

Spectacular Log Home with Private Lake Access: This holiday home rental outside of Windsor is located on a lake, 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 dishwasher, a fridge and a stovetop, 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 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.