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Compare 149 Vacation Homes in Windsor with updated reviews, rates, and availability.

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (20)
"We usually rent right near our relatives closer to Newcastle, but there was a problem with heat in property so we needed a new rental to move into and “Otterly getaway” was willing to rent to us the day before they technically were available which was good for us. The kitchen of the getaway is just perfect for cooking side dishes for our large family Thanksgiving that was just about 20 minutes a way. We slept in the king bed and it was excellent sleeping. The heating system kept us also very...
The price is AED 915
AED 1,589 total
includes taxes & fees
7 Jan - 8 January 2025
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (8)
"The stay was a very nice place and we will be coming back with the whole family next time. "
Cozy Long Pond Cottage: private mooring & shared dock

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (237)
"Everything that was promised was fulfilled. Host & caretaker were available and great to deal with. House was welcoming and comfortable in this cold-weather visit. We’d love to return in summer, the lake access clearly is wonderful."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters

9.0 out of 10, Wonderful, (73)
"It was so nice to be next door to family to celebrate our uncle’s 90th birthday. We enjoyed staying in a house with a lot of history. "
Don't miss the Pumpkin Festival weekend filled with lobster dinners and oysters

Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

10.0 out of 10, Exceptional, (3)
"The house is new, absolutely immaculate and filled with light. The fully equipped kitchen was a joy to work in. The proximity to both Belfast and Camden was a huge plus. Our 2 dogs loved the open grassy field! A very friendly neighborhood too."
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.0 out of 10, Very Good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (75)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (40)
"A lovely, clean house with a peaceful view of the water, this was a great choice for a family gathering. We were able to seamlessly host Thanksgiving, with new appliances and so much already provided. The attention to detail and differentiated space made for a great flow. We also traveled with two small kids, and were easily able to adapt. Highly recommend this for a cozy winter space, and I can see how it would be a delight in the summer as well!"
Sunfish Cove is the perfect year round getaway.

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.6 out of 10, Exceptional, (15)
"The house was great in every way. "
The price is AED 496
AED 1,144 total
includes taxes & fees
27 Dec - 28 Dec
Spacious Country Home w/ Hot Tub, near Colby/Thomas

The Modern Maine Retreat

10.0 out of 10, Exceptional, (2)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat

Lake Front with Amazing Sunsets on McGrath Pond

10.0 out of 10, Exceptional, (17)
"Very clean, cute lake house. Owner responsive, everything you need for a rental home. Lake and lake toys were so great! We really enjoyed our stay. Thank you!!! "
Lake Front with Amazing Sunsets on McGrath Pond

4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.

2.0 star property
9.0 out of 10, Wonderful, (4)
"We enjoyed this house with plenty of comfortable spaces for our family! It had all the essentials and a nice Hot Tub to enjoy the cooler weather in. The beds were comfortable, plenty of pillows and extra blankets. The space in the basement was lovely. We did have to be mindful of the water pressure so someone could shower 1 at a time. But overall, this was a beautiful home away from home"
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.

Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

2.0 star property
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

Red Cedar Haven: Lakeside Tranquility

10.0 out of 10, Exceptional, (7)
"This is a lovely spot with expansive views of a gorgeous lake location. We enjoyed the house, the grounds, the upper and lower decks, the kayaks and SUPs provided, and dock with access to the lake. Everything was spotless and highly functional with thoughtful host details like coffee and soaps provided. A great place for family. We’d love to return. "
The price is AED 2,387
AED 4,073 total
includes taxes & fees
24 Dec - 25 Dec
Red Cedar Haven: Lakeside Tranquility

Fantastic two-level home & guest cottage with fast WiFi & lake access - dogs OK

4.0 out of 10, (2)
"The property had enough room for 10 adults to spread out comfortably. The view was beautiful. The larger house is much nicer than smaller cabin. The smaller cabin is very rustic and smells like an old camp. The listing had a fire pit listed but none was provided. The property is steep in some parts and those with limited mobility may have a hard time accessing some of the property."
Fantastic two-level home & guest cottage with fast WiFi & lake access - dogs OK

MoonLight Treehouse- Luxury Waterfront Escape

10.0 out of 10, Exceptional, (17)
"This is a lovely spot to relax and recharge. Just steps away from the stream, which was gorgeous in the fall. Feras and family were excellent hosts. The Moonlight treehouse was thoughtfully decorated; we wish wexould have stayed longer. Excellent proactive communication. We will be going back in the future!"
The price is AED 1,983
AED 3,578 total
includes taxes & fees
30 Dec - 31 Dec
MoonLight Treehouse- Luxury Waterfront Escape

Biscay Repose, Biscay Pond, Bristol. Private, spacious, family friendly

10.0 out of 10, Exceptional, (2)
"My wife and two children stayed at Biscay Repose for two weeks and we absolutely loved our time there! Jill was a superb host. She was always very kind, responsive, and helpful both before and all during our trip. We had asked her if it the house had a crib for our 2-year-old son and, though it didn’t, she went out of her way to locate one for us. She was also very helpful with directions, since Google Maps is not reliable near the house (we discovered that Apple Maps did work well though). The...
Biscay Repose, Biscay Pond, Bristol. Private, spacious, family friendly

Sweeping Sheepscot River views in newly renovated 200 year old Wiscasset home

9.6 out of 10, Exceptional, (10)
"Ok, but no easy contact to inform about poor draining toilet and broken coffee pot. Called someone in India, was disconnected, therefore PIA to communicate with someone about the property. "
Sweeping Sheepscot River views in newly renovated 200 year old Wiscasset home

SkyView Treehouse- Luxury Waterfront Retreat

10.0 out of 10, Exceptional, (3)
"Absolutely stunning home and location. From all the little details in the house and the host always made sure we had everything we needed and that he was just a text away if we needed anything at all. We had use of the kayaks and I would definitely suggest that because the scenery is just beautiful. Feras and his family are great hosts and I highly recommend them. "
The price is AED 1,833
AED 3,392 total
includes taxes & fees
24 Dec - 25 Dec
SkyView Treehouse- Luxury Waterfront Retreat
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 property types in Windsor

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (97)
"We were having a delightful stay until we noticed that there was no heat but from the fire place. Unfortunately, we had to leave in the middle of our stay. Vrbo gave us a refund. I would stay there again. Lovely and sunny. Excellent Property Manager."
A Charming Waterfront Cottage with Touches of Elegance

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.0 out of 10, Very Good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
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.