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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Windsor holiday rentals

Interior

Damariscotta Lakefront Cottage perfect for a relaxing getaway

Damariscotta Lakefront Cottage perfect for a relaxing getaway
Jefferson
The price is HK$2,744
HK$5,863 total
includes taxes & fees
2 Aug - 3 Aug
Damariscotta Lakefront Cottage perfect for a relaxing getaway
Property grounds

Luxury Lakefront Cabin in Hope - Close to Camden & Rockland

Luxury Lakefront Cabin in Hope - Close to Camden & Rockland
Hope
10.0 out of 10, Exceptional, (1 review)
"Jen was very communicative…responding in minutes! The cabin was lovely and very comfortable. Our youngest son spent the afternoon and following morning fishing off the dock and loved the s’more fixings. My husband took out the kayak and just relaxed by reading and taking in the tranquil setting. Our oldest loved hanging in his nook. I took advantage of the washer/dryer but also enjoyed a glass of wine and the old school records. The beds were very comfortable, and the master bedroom was...
United States
Lauren E.
The price is HK$5,096
HK$8,299 total
includes taxes & fees
9 Aug - 10 Aug
Luxury Lakefront Cabin in Hope - Close to Camden & Rockland
Exterior

Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm
Union
9.6 out of 10, Exceptional, (18 reviews)
"We had never stayed in a yurt before and this one had everything you need. We ate breakfast out on the deck and enjoyed the scenery. We had a really nice time!"
United States
Karen I.
The price is HK$1,451
HK$2,168 total
includes taxes & fees
22 Jul - 23 Jul
Dome 1 - Luxury Dome at Come Spring Farm
WiFi

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Union
8.4 out of 10, Very good, (9 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is HK$1,568
HK$2,227 total
includes taxes & fees
23 Jul - 24 Jul
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Interior

Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
10.0 out of 10, Exceptional, (3 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is HK$1,764
HK$2,590 total
includes taxes & fees
26 Jul - 27 Jul
Come Spring Farm Airstream , Lake & farm animals
WiFi

Come Spring Farm Glamping Dome 2

Come Spring Farm Glamping Dome 2
Union
5.6 out of 10, (4 reviews)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
United States
Healy C.
The price is HK$1,451
HK$2,081 total
includes taxes & fees
22 Jul - 23 Jul
Come Spring Farm Glamping Dome 2
Interior

Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
9.0 out of 10, Wonderful, (2 reviews)
"I liked that it was by the lake quiet and secluded. "
United States
Wilma
The price is HK$1,129
HK$3,165 total
includes taxes & fees
16 Aug - 17 Aug
Rustic Retreat Across From Lake; Family Friendly!
Property grounds

Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
10.0 out of 10, Exceptional, (3 reviews)
"Really great place….very thoughtful set up for us to enjoy."
United States
Peter P.
The price is HK$1,011
HK$1,273 total
includes taxes & fees
22 Jul - 23 Jul
Glamping at Maine Water Buffalo Farm
Exterior

The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
The price is HK$6,939
HK$10,204 total
includes taxes & fees
5 Aug - 6 Aug
The Entire Waldoboro Inn
Property grounds

Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (19 reviews)
"Great location for visiting the coast."
United States
Sallie S.
The price is HK$862
HK$3,239 total
includes taxes & fees
16 Aug - 17 Aug
Rustic Retreat Across from Lake; Family Friendly!
Coffee/tea maker, fridge, microwave, stovetop

Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (26 reviews)
"We had a lovely time in Maine and enjoyed the farm house for our downtime and sleeping. It was exactly what we were looking for and would 100% stay here again and recommend it to others. Thank you!"
United States
Carrie Plympton F.
The price is HK$1,074
HK$3,940 total
includes taxes & fees
9 Aug - 10 Aug
Near Lakes, Bay & Trails! Historic Waldoboro Gem
TV

Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is HK$2,456
HK$4,224 total
includes taxes & fees
8 Aug - 9 Aug
Once Upon a Time — A Peaceful Maine Escape
Interior

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (44 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
The price is HK$1,952
HK$3,410 total
includes taxes & fees
20 Aug - 21 Aug
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

Discover Coastal charm, just a quick 26-min drive away

Discover Coastal charm, just a quick 26-min drive away
Damariscotta
10.0 out of 10, Exceptional, (22 reviews)
"Lovely, small cottage. Very convenient to Main Street shops. A great coffee shop just across the street! The outside garden area is particularly charming for relaxing and reading. Host was friendly and readily available."
United States
June I.
The price is HK$2,313
HK$2,872 total
includes taxes & fees
29 Jul - 30 Jul
Discover Coastal charm, just a quick 26-min drive away
Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
8.6 out of 10, Excellent, (4 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
The price is HK$1,411
HK$1,760 total
includes taxes & fees
19 Aug - 20 Aug
Peaceful Intown Studio ~ Walk to Shops & Dining
Exterior

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
The price is HK$1,309
HK$2,480 total
includes taxes & fees
28 Jul - 29 Jul
Spacious 1 Bedroom Cottage Close to Everything 3
Front of property

Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
United States
Deborah
The price is HK$1,419
HK$3,847 total
includes taxes & fees
9 Aug - 10 Aug
Near Lakes, Bay & Trails! Historic Waldoboro Gem
2 bedrooms, iron/ironing board, bed sheets

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (4 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is HK$917
HK$2,010 total
includes taxes & fees
22 Jul - 23 Jul
Cheerful Cottage with Loft 9
1 bedroom, iron/ironing board, bed sheets

Cheerful Cottage Close to Everything 13

Cheerful Cottage Close to Everything 13
Edgecomb
9.2 out of 10, Wonderful, (17 reviews)
"Nice and quiet even though it was right next to major travel routes "
United States
Gary
The price is HK$980
HK$2,087 total
includes taxes & fees
26 Jul - 27 Jul
Cheerful Cottage Close to Everything 13
Outdoor dining

Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is HK$862
HK$1,864 total
includes taxes & fees
11 Aug - 12 Aug
Happy Cottage Near Everything 11
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

Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

8/10 Good
"Very good location and great sunsets out the balconies or just drive down to the water for beautiful shots. Room was clean and comfortable, if a bit basic. The loveseat was extremely uncomfortable. Breakfast was basic but staff were friendly."
CHARLENE 1-night trip
Posted 8 hours ago
Cod Cove Inn, BW Signature Collection

Find out more about Windsor

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

Frequently asked questions

Are there holiday rentals 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. Windsor is known for its shopping and restaurants.

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

Nestled in Nobleboro: This holiday home rental outside of Windsor is located next to a golf course, and has a patio, a garden and laundry facilities to put you at ease in your new surroundings.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Maine State Museum, or get outside and enjoy nature at Threemile Pond. In the wider area, you’ll find Old Fort Western and Capitol Park.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.