Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Outdoor family fun on beautiful Messer Pond - 11 miles from Mt Sunapee!

10.0 out of 10, Exceptional, (25)
"Great location! Close to town but felt relaxed and peaceful. Would definitely look to rent this house again."
Outdoor family fun on beautiful Messer Pond - 11 miles from Mt Sunapee!

Rustic Waterfront Cottage w/ Fire Pit & Kayaks

2.5 star property
Rustic Waterfront Cottage w/ Fire Pit & Kayaks

Cozy Lakeside Year Round Retreat ☀️🛶 🎣 🏊 🍁 🎃 🍎 🎿🏂 ❄️ & 🐾 are welcome 😊

9.8 out of 10, Exceptional, (18)
"Very clean, all the comforts of home. We loved sitting out and enjoying the lake."
Cozy Lakeside Year Round Retreat ☀️🛶 🎣 🏊 🍁 🎃 🍎 🎿🏂 ❄️ & 🐾 are welcome 😊

Lakefront Cabin w/ Panoramic Water View & Access

9.4 out of 10, Exceptional, (8)
"Overall good rental but these are 3 minor issues: 1. A railing from the parking lot to the front door would help to walk down the steps. 2. Additional bath towels and wash clothes are needed. 3. A large stone is missing from the last deck step to the dock."
Lakefront Cabin w/ Panoramic Water View & Access

Cozy cottage on Pleasant Pond

9.6 out of 10, Exceptional, (19)
"Stayed in the winter, place got a bit cold (it does not have central heat). Wasn’t a lighter or enough firewood for our stay but the host brought a lighter and more wood. Beautiful pond in the back and the location is good, with easy access to the highway. Neighbors were close by, we were asked to turn off the outdoor light because it was shining into their house. Cottage was clean. There are security cameras outside. Overall it is a cozy place to stay in a good area. "
Cozy cottage on Pleasant Pond

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

10.0 out of 10, Exceptional, (13)
"To a person (ages 9-80) we all were very happy with your Lovely vacation home. The space is conducive to being alone or all together, it truly does not show as well online as it is in person. The one mile drive to Mt Sunapee could not be better. Everyone is looking forward to a future trip there. blessings to you in 2025"
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

Sunapee Gathering Place, Serene Restored Barn

10.0 out of 10, Exceptional, (10)
"I was here with my girls and their kids to visit my mom and my sister who live in NH and havent got to visit in 4 yrs. Was the perfect space for everyone to visit and spend time together. Everything was perfect as far as space and beauty and luxury."
Sunapee Gathering Place, Serene Restored Barn

Lake Sunapee Cozy Cottage - Blodgett Landing

9.6 out of 10, Exceptional, (45)
"My wife, our two dogs, and I, had a lovely few days at Grey Gables. The cottage was clean, cozy, and only steps from the lake, private dock, and sitting area. Communication was excellent. We will definitely be back. "
Lake Sunapee Cozy Cottage - Blodgett Landing

Pristine Waterfront, Charming Home, Breathtaking Views

9.8 out of 10, Exceptional, (56)
"Beautiful leaves in reds, oranges, and yellows reflected in a gorgeous pond with a pair of loons slowly floating by....Perfection! What a gorgeous location! We had a great stay- the kitchen was wonderful to cook in- we loved the gas stove- bacon tasted so delicious with croissants in the morning! The house is large and comfortable- cozy couch, large piano, washer and dryer, tv, and wifi. We have to agree with other guests- the bed is squeaky....ridiculously squeaky.....to the point of...
Pristine Waterfront, Charming Home, Breathtaking Views

Boutique Cottage | Patio & Fire Pit | Deck w/ View

10.0 out of 10, Exceptional, (95)
"Very nice place and very nice hosts. Would definitely stay again!"
Boutique Cottage | Patio & Fire Pit | Deck w/ View

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

10.0 out of 10, Exceptional, (65)
"My husband, myself, 3 of my adult kids and 5 grandchildren under 7 stayed very comfortably. So many nice rooms. Although very updated had a very nostalgic feel. All of the living spaces were extra large and plenty of seating. The kitchen had everything that we needed and the yard was humongous. We were fortunate to get snow while we were there and the kids had never seen snow since we’re from Georgia. It was a wonderful stay. Thank you so much, Wayne. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Modern Francestown Retreat on Scobie Pond!

10.0 out of 10, Exceptional, (5)
"Fairly new house on the pond. Little sand beach. Canoe, paddle board and kayaks (need new/more paddles). Spacious. Large, well appointed and supplied modern kitchen. Nice master suite. Only one bathroom on ground floor for 3 bedrooms. Plenty of bench seating on deck facing lake, but could use use some chairs with cushions. "
Modern Francestown Retreat on Scobie Pond!

Panoramic Water Views, waterfront house on French pond

9.2 out of 10, Wonderful, (10)
"The charming home is very remote and private. Updated kitchen and bathroom providing all amenities you could want. Comfortable beds, but master is very tall. Although the living area futon seating provides extra sleeping options, they are not the most comfortable for sitting/lounging. A softer chair or two would be welcome. Lovely deck for lake watching. Frogs aplenty!"
Panoramic Water Views, waterfront house on French pond

SPACIOUS Custom 5 Bed Home Minutes to Mt.Sunapee! Garage, Hot Tub, Game Room!

10.0 out of 10, Exceptional, (21)
"The house was exactly what we needed. "
SPACIOUS Custom 5 Bed Home Minutes to Mt.Sunapee! Garage, Hot Tub, Game Room!

Cozy Camp in the woods surrounded by nature.!

10.0 out of 10, Exceptional, (11)
"Beautiful setting, quiet, bucolic. Cabin super clean and rustic. Well equipped, clean gym. Owners are super and very kind. A "
Cozy Camp in the woods surrounded by nature.!

Beautiful Private Lakefront new Log Home

9.8 out of 10, Exceptional, (49)
"We recently stayed at this property for Thanksgiving with nine adults, two children, and two well-behaved dogs, and had a memorable experience overall. The home is set in a stunning location with a beautiful yard, lake, and deck space that we thoroughly enjoyed. Outdoor highlights included making s’mores over the solo fire pit and using the pizza oven. Inside, the two kitchens were impressively stocked with cookware, appliances (including two coffee makers and an espresso machine), and...
Beautiful Private Lakefront new Log Home

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.

9.8 out of 10, Exceptional, (79)
"The house - or as it was referred to by some the castle - was awesome. We truly enjoyed our stay. "
HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.

Breathtaking Newbury Cottage w/ Deck on Chalk Pond

9.6 out of 10, Exceptional, (46)
"My friend and I enjoyed our stay. The only issue was the thermostat controlling the stove. It was either too cold or too hot. Maybe more specific instructions for operation. Thanks for the stay!"
Breathtaking Newbury Cottage w/ Deck on Chalk Pond

Relaxing Hot Tub Getaway

10.0 out of 10, Exceptional, (11)
"Very nice house that was clean and had very nice Activities like hot tub games etc Definitely would come back and stay again. Rebecca is a very good host "
The price is €288
includes taxes & fees
23 Jan - 24 Jan
Relaxing Hot Tub Getaway

Quaint Dunbarton Waterfront Cottage

9.4 out of 10, Exceptional, (46)
"LOVELY AND PEACEFULVERY KIND HOST."
Quaint Dunbarton Waterfront Cottage
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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Other types of properties in Windsor you may be interested in

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (979)
"Clean and quiet:)"
The price is €98
includes taxes & fees
2 Feb - 3 Feb
Days Inn by Wyndham Keene NH

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (276)
"Nice simple and modern. Great customer service. Check in and out was simple and quick. Unfortunately pool wasnt open but guests where advised the Best Western across the way was allowing their guests to show room cards to be able to use the pool their facility. Clean rooms but no laundry amenities available. Had a great stay. But whiling using the side door my wife notcied the levels on the walk way were not defined and walking thru at night time could create an emergency for another guest....
The price is €143
includes taxes & fees
9 Feb - 10 Feb
Hampton Inn & Suites Keene

Bluebird Sunapee

3.0 star property
8.8 out of 10, Excellent, (634)
"."
Bluebird Sunapee
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.

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?

Cozy Lakeside Year Round Retreat ☀️🛶 🎣 🏊 🍁 🎃 🍎 🎿🏂 ❄️ & 🐾 are welcome 😊: This holiday home rental outside of Windsor is located on a lake, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Highland Lake. In the wider area, you’ll find Nubanusit Lake and Pats Peak.

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.