Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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 😊

Chic Farmhouse Decor | Deck w/View

10.0 out of 10, Exceptional, (46)
"Interior, comfort, everything we needed - house had it. Location is super cool aswell. Welcome bottle of red wine was a nice surprise !:)"
The price is €392
includes taxes & fees
3 Dec - 4 Dec
Chic Farmhouse Decor | Deck w/View

Lakefront Bradford Cottage w/ Dock, Near Skiing!

9.6 out of 10, Exceptional, (5)
"This cottage was very snug for a chilly week’s stay during glorious fall foliage time. We enjoyed the abundance or natural light with the skylights and many windows and views of the small lake. A quiet and comfortable home base for many day trips and a well-equipped kitchen for breakfasts and dinners at home. "
Lakefront Bradford Cottage w/ Dock, Near Skiing!

Rustic Waterfront Cottage w/ Fire Pit & Kayaks

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

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

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!

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

Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

10.0 out of 10, Exceptional, (5)
"Beautiful property, professional and helpful hosts, clean and spacious, bountiful amenities and a great night with friends!"
The price is €1,084
includes taxes & fees
12 Dec - 13 Dec
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

10.0 out of 10, Exceptional, (156)
"The home perfect for our needs. Plenty of room and a GREAT view of the back of Mount Sunapee. The neighborhood is very nice and quiet. The kitchen was well equipped. We had a great time! Thank you!"
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

9.8 out of 10, Exceptional, (24)
"We had a lovely time at this property. Very cute cabin feel, perfect for the fall. We were in town for a wedding at Pats Peak and were able to walk to the venue. The host had a fire going for us when we arrived and the cabin was peak coziness! As other reviews mentioned the hosts house is right there but it still felt private. Thanks for a great stay! "
Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

Beautiful lakefront Summer Lake House & Ski Cottage near Mt. Sunapee

9.6 out of 10, Exceptional, (30)
"We had an amazing time,the weather was the best i can remember for peak foliage time. I wish the Bass were more cooperative but the ones we got were quality."
Beautiful lakefront Summer Lake House & Ski Cottage near Mt. Sunapee

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!

Cozy cottage on Pleasant Pond

9.6 out of 10, Exceptional, (18)
"Had a great stay, home is very cozy and the pond out back is beautiful. Great place to take a little break"
Cozy cottage on Pleasant Pond

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

10.0 out of 10, Exceptional, (12)
"The hosts were extremely communicative and beyond helpful for our stay. We let them know that we were staying and planning on using the VRBO for getting ready for my wedding on the weekend. I appreciate their communication and the layout of the home. Their directions and tips were very helpful and made the stay very helpful. Thank you all so much - this was one of the least stressful parts about my wedding. "
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

SPACIOUS Custom 5 Bed Home Minutes to Lake Sunapee! Garage, Hot Tub, Pool Table!

10.0 out of 10, Exceptional, (19)
"It was so amazing! Everything was beautiful and so clean! "
SPACIOUS Custom 5 Bed Home Minutes to Lake Sunapee! Garage, Hot Tub, Pool Table!

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, (48)
"This was our second time renting this house. We love the location and everything about it. We have a large family and the house is more than big enough for everyone and the lake is beautiful."
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, (78)
"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 €277
includes taxes & fees
1 Dec - 2 Dec
Relaxing Hot Tub Getaway
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

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (994)
"Well appointments room, very spacious and quiet. Fan I bathroom did not work "
The price is €112
includes taxes & fees
22 Dec - 23 Dec
Courtyard by Marriott Keene Downtown

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (256)
"The staff are friendly and helpful; our room was quiet, clean and bed very comfortable. Our room had ample space for suitcases, hooks to hang jackets and hooks in bathroom for our towels. Lots of space to spread out our belongings. Very good breakfast, comfortable seating. An overall enjoyable stay when visiting family in Keene. We will definitely stay there again."
The price is €138
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Keene

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (963)
"Great rooms and service love it my favorite place to stay in Keene "
The price is €81
includes taxes & fees
23 Dec - 24 Dec
Days Inn by Wyndham Keene NH
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 Friendly Farm, or get out into nature at a spot like Highland Lake. In the wider area, you’ll find Contoocook River 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.