Holiday Rentals in Windsor

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Windsor

Exterior
Lakefront Cabin in Beautiful, Quiet Location
Lakefront Cabin in Beautiful, Quiet Location
8.0 out of 10, Very good, (4)
"We were there in mid July on a hot week. We loved the privacy and how quiet the property was! We spent most days down on the dock, swimming and fishing. The living room has a window that is wall sized and swings open to allow a breeze of the pond which was great in the evening. We did not have any issues with bugs entering the cabin during our stay. The cabin brought back childhood memories of camp and sitting on the deck or by the fire at sunset each day was amazing. We enjoyed drinks by the...
Lakefront Cabin in Beautiful, Quiet Location
Property grounds
Owl's Nest Treehouse
Owl's Nest Treehouse
10.0 out of 10, Exceptional, (11)
"This place is beautiful! It had everything we needed. The hosts were very communicative and encouraged us to contact them if we had any questions. We stayed at the treehouse to celebrate our 30th anniversary and it exceeded our expectations. I would highly recommend this cozy and quiet retreat."
The price is €296
includes taxes & fees
21 Oct - 22 Oct
Owl's Nest Treehouse
Miscellaneous
Private Beach And Mountain Lake Home
Private Beach And Mountain Lake Home
9.6 out of 10, Exceptional, (123)
"I loved the house with so many bits of history of times past. It was also nice that it had just about anything you could possibly need which makes packing less stressful. I would have loved to k ow more about the artwork that adorns the walls and yard. I felt very much at peace while there."
Private Beach And Mountain Lake Home
Property grounds
Quaint Dunbarton Waterfront Cottage
Quaint Dunbarton Waterfront Cottage
9.4 out of 10, Exceptional, (53)
"Great time at this quite little getaway. It was a hidden gem!"
Quaint Dunbarton Waterfront Cottage
Exterior
Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat
Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat
2.0 star property
Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat
Fridge, microwave, oven, stovetop
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.
9.8 out of 10, Exceptional, (27)
"great location"
The price is €158
includes taxes & fees
3 Nov - 4 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Interior
16 ppl 2 hot tubs, game room, fire pit
16 ppl 2 hot tubs, game room, fire pit
9.8 out of 10, Exceptional, (9)
"Clean, lots of space, helpful host, hot tub was also nice"
The price is €474
includes taxes & fees
22 Oct - 23 Oct
16 ppl 2 hot tubs, game room, fire pit
Fridge, microwave, oven, stovetop
Peaceful Mountain View Retreat
Peaceful Mountain View Retreat
9.6 out of 10, Exceptional, (14)
"Perfect ski getaway. We loved Crotched Mountain and the peaceful retreat when we returned back to the property. "
Peaceful Mountain View Retreat
Interior
Private Hot Tub Suite
Private Hot Tub Suite
9.0 out of 10, Wonderful, (8)
"Stayed 3 nights while visiting relatives. Teen loved the Xbox. Had everything we could possibly need. Would definitely stay again."
The price is €227
includes taxes & fees
21 Oct - 22 Oct
Private Hot Tub Suite
Terrace/patio
Unique Cozy private 1-bedroom apartment in charming Temple
Unique Cozy private 1-bedroom apartment in charming Temple
9.8 out of 10, Exceptional, (6)
"The location was a bit hard to find with any online map, it’s not accurate. But with a bit of driving, easily found! It was lovely, peaceful, and cool during a hot weekend so nice and relaxing!"
The price is €377
includes taxes & fees
20 Oct - 21 Oct
Unique Cozy private 1-bedroom apartment in charming Temple
Exterior
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
10.0 out of 10, Exceptional, (28)
"Pristine cabin, even better than the pictures. Enjoyed our peaceful stay in the woods."
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Fridge, microwave, oven, stovetop
Chic Farmhouse Decor | Deck w/View
Chic Farmhouse Decor | Deck w/View
10.0 out of 10, Exceptional, (51)
"Great cabin about 2 minutes from Mt. Sunapee resort and state park, as well as several lake towns. Beds are extra comfortable and the kitchen has everything we needed. "
The price is €383
includes taxes & fees
16 Oct - 17 Oct
Chic Farmhouse Decor | Deck w/View
Fridge, microwave, oven, stovetop
HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.
HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.
9.8 out of 10, Exceptional, (87)
"Beautiful place with lots of room for a family vacation Kitchen well stocked with useful items: big pans, microwave, gas stove , 2 ovens and 2 dishwashers.No a/c, but we made it work with their fans and some we brought. Lots of things to do with kids in the are"
HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.
Smart TV, fireplace, Netflix, books
Harbor House: Sleeps 20, Fireplace, 2 TVs, 2 kitchens, walk to restaurants/bars
Harbor House: Sleeps 20, Fireplace, 2 TVs, 2 kitchens, walk to restaurants/bars
9.6 out of 10, Exceptional, (27)
"This space was great for our large family attending a nearby wedding. The large table and living space was exactly what we were hoping for. All bedrooms were comfortable and adequate. "
Harbor House: Sleeps 20, Fireplace, 2 TVs, 2 kitchens, walk to restaurants/bars
Exterior
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
9.6 out of 10, Exceptional, (23)
"Great get away on lake Sunapee, great house just a short walk to the lake. Great place to relax and take in the sun set on the dock or grilling on the deck. Well equipped home that is super clean,just a great getaway. "
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Exterior
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
10.0 out of 10, Exceptional, (9)
"Very spacious, with beautiful amenities and very friendly hosts!"
The price is €921
includes taxes & fees
16 Oct - 17 Oct
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Outdoor pool
Ski Minutes Away & Pool Onsite
Ski Minutes Away & Pool Onsite
10.0 out of 10, Exceptional, (9)
"We enjoyed the property very much. The pool was amazing! The kitchen was well equipped and the communication with the owner was very good. Great location to downtown for restaurants and grocery store"
Ski Minutes Away & Pool Onsite
Interior
Sunapee Barn Retreat
Sunapee Barn Retreat
10.0 out of 10, Exceptional, (17)
"very excessive and well equiped"
Sunapee Barn Retreat
TV, books, music library, video library
Spectacular Log Home with Private Lake Access
Spectacular Log Home with Private Lake Access
10.0 out of 10, Exceptional, (106)
"Great location and beautiful house! Thank you! "
Spectacular Log Home with Private Lake Access
Interior
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
10.0 out of 10, Exceptional, (7)
"We had the most amazing stay at Leah and Chris’s beautiful home! From the moment we arrived, we were blown away by how clean, spacious, and thoughtfully stocked the house was—it truly had everything we could possibly need and more.Our group of 12 (including young kids and dogs!) had tons of space to spread out comfortably, and every single bed was super cozy. The huge yard was perfect for lawn games, which were conveniently provided, and we spent hours outside enjoying the privacy and peaceful...
The price is €960
includes taxes & fees
16 Oct - 17 Oct
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Room was clean and staff was friendly. "
Britney 1-night trip
Posted 5 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €158 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 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?

Private Beach And Mountain Lake Home: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday 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.