Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Washington

4.95 out of 5 average rating, 130 reviews

Fox and Bird Retreat on Davis Stream

Our off-the-grid, solar-powered cottage is nestled within our 18 acres in the town of Washington, Maine. The cottage borders a beautiful stream, is surrounded by tall pines and is several hundred feet away from our home, providing a very private and serene experience. Guests can wander or snowshoe on our property, relax in the screen house next to the cottage or hang by the accessible fire pit. We are close to many local lakes and hiking trails and only 30 minutes from Camden & Rockland.

Sep 3 – 10

$109 per night
Guest favorite

Apartment in Richmond

4.88 out of 5 average rating, 156 reviews

Designers Dream 1br Apt where class meets relax!!!

This Designers Dream 1br apartment is located in the quintessential small Maine town of Richmond. Open the door feast your eyes on this truly unique and beautiful spot and get ready to relax or explore! Richmond is home of Swan Island a great spot to explore via kayak or canoe or just grab the ferry! We're 45 min to all downtown Portland has to offer. We are an hour to Booth Bay Harbor and the beautiful botanical gardens. Popham beach is 45 min away, one of the most amazing beaches in state.

Sep 23 – 30

$100 per night
Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 110 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Feb 13 – 20

$104 per night

Popular amenities for Windsor vacation rentals

Other great vacation rentals in Windsor

Guest favorite

Home in Augusta

5.0 out of 5 average rating, 10 reviews

Super cute waterfront cottage

Sep 12 – 19

$124 per night
Guest favorite

Cottage in Augusta

5.0 out of 5 average rating, 80 reviews

Modern Hideaway in Augusta

Apr 28 – May 5

$92 per night
Guest favorite

Cottage in China

4.99 out of 5 average rating, 77 reviews

Lake House on Three Mile Pond with Amazing views

May 4 – 11

$155 per night
Guest favorite

Cabin in Whitefield

5.0 out of 5 average rating, 55 reviews

Tiny Cabin on 100 acres

Nov 20 – 27

$116 per night
Guest favorite

Cabin in Augusta

5.0 out of 5 average rating, 15 reviews

Quintessential Maine cabin w/ private waterfront

Oct 17 – 24

$299 per night
Guest favorite

Cottage in Whitefield

4.96 out of 5 average rating, 54 reviews

Ollie's Cottage on the Sheepscot River

Oct 10 – 17

$166 per night
Guest favorite

Guest suite in Hallowell

5.0 out of 5 average rating, 49 reviews

Welcome to the Brown House! Hallowell studio

Nov 11 – 18

$67 per night
Guest favorite

Apartment in Palermo

4.98 out of 5 average rating, 88 reviews

One bedroom apartment in rural Waldo County, Maine

Sep 17 – 24

$83 per night
Guest favorite

Apartment in Augusta

4.94 out of 5 average rating, 53 reviews

Downtown Augusta Studio - Newly Renovated #3

May 27 – Jun 3

$82 per night
Guest favorite

Guesthouse in Appleton

4.99 out of 5 average rating, 72 reviews

BirdNest Studio: Sunny, Rustic Guesthouse & Garden

Oct 25 – Nov 1

$115 per night
Guest favorite

Apartment in Hallowell

4.95 out of 5 average rating, 22 reviews

The Gallery

Nov 28 – Dec 5

$123 per night
Guest favorite

Home in Waldoboro

4.98 out of 5 average rating, 61 reviews

1830s Cape hosted by George & Paul

Nov 19 – 26

$86 per night

Destinations to explore

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  5. Windsor