Title: Windsor Vacation Rentals from $269: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=175568&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=175568&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=175568&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=175568&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor vacation rentals

![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/0450d353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/d8ba6715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/3ff0e36f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112739/2e3e136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lighthouse Lane

[](https://www.expedia.com/Augusta-Hotels-Cottage-On-Cobbosseecontelake.h63112739.Hotel-Information)

Manchester

10/10

Exceptional

(70 reviews)

"Very nice stay Beautiful lake views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karen G.

$286 nightly

$312 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Augusta-Hotels-Cottage-On-Cobbosseecontelake.h63112739.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/3d25364d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/d71068b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/c6360210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76970000/76965000/76964979/71b4e138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ice Fishing, Dog Friendly, Lake Great Pond

[](https://www.expedia.com/Belgrade-Hotels-NEW-Cozy-3-Bedroom-Cottage-On-Great-Pond-Dog-Friendly.h76964979.Hotel-Information)

Belgrade

10/10

Exceptional

(50 reviews)

"All was exactly as we hoped it would be, perfect for a family and added benefit of pet friendly."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jonathan I.

$359 nightly

$391 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Belgrade-Hotels-NEW-Cozy-3-Bedroom-Cottage-On-Great-Pond-Dog-Friendly.h76964979.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102400000/102392200/102392135/8e44fdce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102400000/102392200/102392135/dd2bd6e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102400000/102392200/102392135/641fc24a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/103000000/102400000/102392200/102392135/c757e939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront 2br/2ba cottage 

[](https://www.expedia.com/Gardiner-Hotels-Waterfront-2br2ba-Cottage.h102392135.Hotel-Information)

West Gardiner

9.8/10

Exceptional

(16 reviews)

"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bruce J.

$333 nightly

$363 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Gardiner-Hotels-Waterfront-2br2ba-Cottage.h102392135.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/4b703bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/17a87d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/e447dc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/f7212acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy getaway: farmhouse with wood stove & jacuzzi tub

[](https://www.expedia.com/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information)

Oakland

10/10

Exceptional

(9 reviews)

"It was that was said to be The host was very nice and helpful . I enjoyed my stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea C.

$345 nightly

$367 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Cozy-Farm-Stay-Pet-Friendly-Peaceful.h113522019.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/815a3cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/w1188h800x0y0-be52bc8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, offices](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/a13047f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105760000/105755000/105754901/73ce4a3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family's Paradise: 3BR/2BA,Game Room & Lake Access

[](https://www.expedia.com/Belgrade-Hotels-A-Familys-Paradise-Spacious-3BR2BA-W-Game-Room.h105754901.Hotel-Information)

Belgrade

9.8/10

Exceptional

(9 reviews)

"We enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tyson W.

$747 nightly

$814 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Belgrade-Hotels-A-Familys-Paradise-Spacious-3BR2BA-W-Game-Room.h105754901.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/87772848.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/60fb6e31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/464ce340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89660000/89655600/89655519/w651h433x0y5-e9133719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilltop 3BR Getaway w/ Chef BBQ, Fire Pit, Patios & Room to Relax

[](https://www.expedia.com/Waldoboro-Hotels-Hilltop-3BR-Getaway-W-Chef-BBQ.h89655519.Hotel-Information)

Waldoboro

9.6/10

Exceptional

(9 reviews)

"Good visit overall."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gerald S.

$590 nightly

$643 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Waldoboro-Hotels-Hilltop-3BR-Getaway-W-Chef-BBQ.h89655519.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/8e06d5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/75c4bc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/54cc436c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33954800/33954758/7cac22ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two bedroom Mid Century Modern apartment in Downtown Hallowell

[](https://www.expedia.com/Augusta-Hotels-Two-Bedroom-Mid-Century-Modern-Apartment-In-Downtown-Hallowell.h33954758.Hotel-Information)

Hallowell

10/10

Exceptional

(82 reviews)

"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rebekah B.

$211 nightly

$230 total

Feb 22 - Feb 23

Total with taxes and fees

[](https://www.expedia.com/Augusta-Hotels-Two-Bedroom-Mid-Century-Modern-Apartment-In-Downtown-Hallowell.h33954758.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/515b6a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/576b2944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/effc1142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/108000000/107720000/107715600/107715523/76608187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming cabin in the birches right on the atv trail!

[](https://www.expedia.com/Fairfield-Hotels-Charming-Cabin-In-The-Birches-Right-On-The-Atv-Trail.h107715523.Hotel-Information)

Fairfield

9.0/10

Wonderful

(6 reviews)

"Very neat cabin. Spacious all utilities and a fire pit"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa O.

$135 nightly

$147 total

Feb 21 - Feb 22

Total with taxes and fees

[](https://www.expedia.com/Fairfield-Hotels-Charming-Cabin-In-The-Birches-Right-On-The-Atv-Trail.h107715523.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/2106c4ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/b382c1a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/68cf4729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118490000/118481900/118481811/e8e22159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

[](https://www.expedia.com/Oakland-Hotels-NEW-Cozy-Cabin-Located-In-Oakland-Tucked-Away-In-A-Peaceful-Wooded-Scene.h118481811.Hotel-Information)

Oakland

$270 nightly

$294 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-NEW-Cozy-Cabin-Located-In-Oakland-Tucked-Away-In-A-Peaceful-Wooded-Scene.h118481811.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/ae0a6cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/af7f3a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/d18cb0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/97000000/96110000/96107000/96106993/9eb8a155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 7BR Hilltop Retreat · 2 Kitchens, Decks & Fire

[](https://www.expedia.com/Waldoboro-Hotels-7BR-Hilltop-Retreat-2-Kitchens-Decks.h96106993.Hotel-Information)

Waldoboro

9.6/10

Exceptional

(5 reviews)

"The house and location was perfect, sitting around the fire pit to end the night was perfect "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

william h.

$1,201 nightly

$1,309 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Waldoboro-Hotels-7BR-Hilltop-Retreat-2-Kitchens-Decks.h96106993.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/6d9c5823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/61a45d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/9ab13d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121860000/121853200/121853117/7a52224f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Intown Studio \~ Walk to Shops & Dining

[](https://www.expedia.com/Newcastle-Hotels-Peaceful-Intown-Studio-Walk-To-Shops-Dining.h121853117.Hotel-Information)

Newcastle

7.0/10

Good

(2 reviews)

"The rental was exceptionally clean and neat. All appliances were like new. Parking was great. The bathroom could’ve used a plug in heater. We could easily hear people walking around on space above us. Nice views "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason R.

$166 nightly

$181 total

Feb 17 - Feb 18

Total with taxes and fees

[](https://www.expedia.com/Newcastle-Hotels-Peaceful-Intown-Studio-Walk-To-Shops-Dining.h121853117.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/7723a7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/479ba3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/58ab669e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/119000000/118940000/118939100/118939094/7cfe1482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Home in Central Maine

[](https://www.expedia.com/Augusta-Hotels-The-Maine-Experience-Where-Expansive-Nature-Meets-Modern-Comfort.h118939094.Hotel-Information)

Sidney

8.0/10

Very Good

(4 reviews)

"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pat D.

$370 nightly

$403 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Augusta-Hotels-The-Maine-Experience-Where-Expansive-Nature-Meets-Modern-Comfort.h118939094.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/129d87e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/db1800b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/acce8344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/58000000/57700000/57698800/57698782/5be70f30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cottage on water's edge of Lake Cobbosseecontee

[](https://www.expedia.com/Manchester-Hotels-Cozy-Cottage-On-Waters-Edge-Of-Lake-Cobbosseecontee.h57698782.Hotel-Information)

Manchester

8.8/10

Excellent

(19 reviews)

"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie P.

$309 nightly

$337 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Manchester-Hotels-Cozy-Cottage-On-Waters-Edge-Of-Lake-Cobbosseecontee.h57698782.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430319/7462c453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430319/b19c689c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430319/996a224b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103430400/103430319/2f6732dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camp Lintonia on Tacoma Lakes

[](https://www.expedia.com/Litchfield-Hotels-COMING-SOONCamp-Lintonia.h103430319.Hotel-Information)

Litchfield

10/10

Exceptional

(12 reviews)

"Booked this property for a girls trip and this property was stunning! Wish we would’ve booked for more days! Ample space for everyone, views were amazing, and the house was gorgeous! Already considering booking again next year! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emma B.

$247 nightly

$269 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Litchfield-Hotels-COMING-SOONCamp-Lintonia.h103430319.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/ea4831c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/43a37948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/445432e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/de936a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The heart of the Belgrade Lakes 

[](https://www.expedia.com/Oakland-Hotels-The-Heart-Of-The-Belgrade-Lakes.h107166584.Hotel-Information)

Oakland

9.0/10

Wonderful

(9 reviews)

"Host was very accommodating "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maureen

$176 nightly

$191 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-The-Heart-Of-The-Belgrade-Lakes.h107166584.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/1d81fc0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/3d43d563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/02a26a70_edited_16e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107420000/107414500/107414470/24687d8e_edited_120b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Discover Oakland charm near Colby College 10 min

[](https://www.expedia.com/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.Hotel-Information)

Oakland

10/10

Exceptional

(6 reviews)

"Very clean and comfy. A pleasure to stay there. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Vicki W.

$236 nightly

$257 total

Feb 16 - Feb 17

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Oakland-Condo-Furnished-2-Bdrm-1-Bath-Newly-Built.h107414470.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/a00de8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/c86c7808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/b1aad0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, books](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/5408df77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sister A-Frame in Woods B

[](https://www.expedia.com/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.Hotel-Information)

Oakland

10/10

Exceptional

(9 reviews)

"Great stay. Would stay here again if in the area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda M.

$225 nightly

$245 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/w3024h3351x0y0-28e12c91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/aa47261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/62f061f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/104000000/103900000/103899900/103899892/3a4f8cb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

[](https://www.expedia.com/Whitefield-Hotels-Studio-Apt-100-Acres-With-KayakCanoePaddleboards.h103899892.Hotel-Information)

Whitefield

10/10

Exceptional

(6 reviews)

"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sandra L.

$260 nightly

$283 total

Feb 20 - Feb 21

Total with taxes and fees

[](https://www.expedia.com/Whitefield-Hotels-Studio-Apt-100-Acres-With-KayakCanoePaddleboards.h103899892.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/126000000/125260000/125253800/125253746/618417fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125260000/125253800/125253746/acdac02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125260000/125253800/125253746/3845b726.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/126000000/125260000/125253800/125253746/8936c08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy newly built 1-bedroom apartment in charming Smithfield

[](https://www.expedia.com/Smithfield-Hotels-Cozy-Newly-Built-1-Bedroom-Apartment-In-Charming-Smithfield.h125253746.Hotel-Information)

Smithfield

$255 nightly

$278 total

Feb 15 - Feb 16

Total with taxes and fees

[](https://www.expedia.com/Smithfield-Hotels-Cozy-Newly-Built-1-Bedroom-Apartment-In-Charming-Smithfield.h125253746.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102640000/102639500/102639493/1cde160c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102640000/102639500/102639493/b6737602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102639500/102639493/da46180d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102640000/102639500/102639493/c6ac2316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Minutes to Colby 

[](https://www.expedia.com/Waterville-Hotels-Minutes-To-Colby.h102639493.Hotel-Information)

Waterville

8.8/10

Excellent

(22 reviews)

"Easy check in and spacious apartment. Excellent location- within minutes of Colby and downtown restaurants. Super comfy living room to relax in after a full day of Parents Weekend:"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jodie M.

$176 nightly

$192 total

Feb 23 - Feb 24

Total with taxes and fees

[](https://www.expedia.com/Waterville-Hotels-Minutes-To-Colby.h102639493.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-27&endDate=2026-02-28&regionId=175568&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Maine%2C+United+States+of+America&regionId=175568&latLong=44.310627%2C-69.580597&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Maine%2C+United+States+of+America&regionId=175568&latLong=44.310627%2C-69.580597&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=VILLA)

Private vacation homes

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Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Maine%2C+United+States+of+America&regionId=175568&latLong=44.310627%2C-69.580597&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Maine%2C+United+States+of+America&regionId=175568&latLong=44.310627%2C-69.580597&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Maine%2C+United+States+of+America&regionId=175568&latLong=44.310627%2C-69.580597&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Maine%2C+United+States+of+America&regionId=175568&latLong=44.310627%2C-69.580597&adults=2&startDate=2026-05-14&d1=2026-05-14&endDate=2026-05-17&d2=2026-05-17&lodging=CHALET)

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## Top Windsor Hotel Reviews

![Hampton Inn Augusta](https://images.trvl-media.com/lodging/6000000/5190000/5185100/5185016/bf2caaca_y.jpg)

### Hampton Inn Augusta

10/10 Excellent

"Clean room, pleasant staff"

[](https://expedia.com/Augusta-Hotels-Hampton-Inn-Augusta.h5185016.Hotel-Information)

![Hampton Inn Waterville](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/3c11b972_y.jpg)

### Hampton Inn Waterville

10/10 Excellent

"The room was conveniently located right off the lobby for my mom as requested and very quiet "

[](https://expedia.com/Augusta-Hotels-Hampton-Inn-Waterville.h721075.Hotel-Information)

![Fireside Inn & Suites Waterville](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a_y.jpg)

### Fireside Inn & Suites Waterville

10/10 Excellent

"Room was very cozy, and staff was pleasant. Loved having governor’s next door. Definitely recommend others to stay."

[](https://expedia.com/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information)

![Lockwood Hotel](https://images.trvl-media.com/lodging/79000000/78100000/78095000/78094968/d4c480e1_y.jpg)

### Lockwood Hotel

10/10 Excellent

"Wonderful setting, terrific staff, and the best accommodations around"

[](https://expedia.com/Waterville-Hotels-Lockwood-Hotel.h78094968.Hotel-Information)

![Maine Evergreen Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/790000/787600/787572/42d3f26f_y.jpg)

### Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent

"The Maine Evergreen was an inspiring Hotel! We travel a lot and believe that is the first time we have used that adjective to convey how we felt about any of the places we have stayed, regardless of price. The room was quite nice. The attached restaurant and lounge was quite cozy and offered high-quality fare. The hotel itself is one giant art gallery with works from dozens of Maine artists on display & for sale. It's in a very convenient location as well. But it was the staff that made our stay most rewarding. We had a very trying trip made even more difficult with car issues and the extreme weather that weekend. But the entire staff eased our anxieties and even offered assistance over and above what we expected. We will certainly choose the Maine Evergreen whenever we are in the Augusta area and give it our highest possible recommendation!"

[](https://expedia.com/Augusta-Hotels-Quality-Inn-Suites-Evergreen-Hotel.h787572.Hotel-Information)

![Best Western Plus Waterville Grand Hotel](https://images.trvl-media.com/lodging/1000000/30000/22100/22003/c76e225a_y.jpg)

### Best Western Plus Waterville Grand Hotel

10/10 Excellent

"Was excellent and pool was heated was wonderful "

[](https://expedia.com/Augusta-Hotels-Best-Western-Plus-Waterville-Grand-Hotel.h22003.Hotel-Information)

![Holiday Inn Express & Suites Waterville - North by IHG](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/d5d283f3_y.jpg)

### Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent

"Clean room, friendly staff and great continental breakfast!"

[](https://expedia.com/Augusta-Hotels-Holiday-Inn-Express-Suites-Waterville-North.h802109.Hotel-Information)

![Senator Inn & Spa](https://images.trvl-media.com/lodging/1000000/10000/9900/9853/19df0ad9_y.jpg)

### Senator Inn & Spa

10/10 Excellent

"I was very satisfied with the hotel and room as it was exactly as represented. There was a difficulty regarding payment at check in which was entirely on me and the girl at the desk was extremely pleasant and helpful as well as patient while I was contacting my bank for release of funds due to fraud activity on my account. She was exceptional and helpful to continue my check in using another credit card and so happy to help. The only negative event was the fire in the kitchen causing me to have to leave my room for over an hour which was inconvenient and cold but no reflection of the hotel just good safety measures in place."

[](https://expedia.com/Augusta-Hotels-Senator-Inn-Spa.h9853.Hotel-Information)

![Days Inn by Wyndham Augusta](https://images.trvl-media.com/lodging/1000000/60000/50600/50552/6adf084b_y.jpg)

### Days Inn by Wyndham Augusta

10/10 Excellent

"The room was clean and staff accommodating. When we had to leave immediately due to the storm overtaking the area, they cancelled the remainder of our reservation without a fuss."

[](https://expedia.com/Augusta-Hotels-Days-Inn-By-Wyndham-Augusta.h50552.Hotel-Information)

## Find out more about Windsor

**Everything you need to know about Windsor vacation rentals**

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

**Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $269 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Windsor rentals**

At Expedia, we put the best Windsor vacation 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 vacation.

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.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Windsor ](https://expedia.com/Windsor-Private-Vacation-Homes.d175568-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Windsor ](https://expedia.com/Windsor-Cottages.d175568-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Windsor ](https://expedia.com/Windsor-Cabins.d175568-aaCabins.Travel-Guide-Accommodation)
- [Apartments in Windsor ](https://expedia.com/Windsor-Apartments.d175568-aaApartments.Travel-Guide-Accommodation)
- [Farmstay in Windsor ](https://expedia.com/Windsor-Agritourism.d175568-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Windsor ](https://expedia.com/Windsor-Bed-And-Breakfast.d175568-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Windsor ](https://expedia.com/Windsor-Houseboats.d175568-aaHouseboats.Travel-Guide-Accommodation)
- [Motels in Windsor ](https://expedia.com/Windsor-Motels.d175568-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Windsor ](https://expedia.com/Windsor-RV-Parks.d175568-aaRVParks.Travel-Guide-Accommodation)
- [Chalets in Windsor ](https://expedia.com/Windsor-Chalets.d175568-aaChalets.Travel-Guide-Accommodation)
- [Resorts in Windsor ](https://expedia.com/Windsor-Resorts.d175568-aaResorts.Travel-Guide-Accommodation)
- [Guest Houses in Windsor ](https://expedia.com/Windsor-Guest-Houses.d175568-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Windsor ](https://expedia.com/Windsor-Villas.d175568-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Windsor ](https://expedia.com/Windsor-Lodges.d175568-aaLodges.Travel-Guide-Accommodation)
- [Condo Rentals in Windsor ](https://expedia.com/Windsor-Condos.d175568-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Windsor?

### What are some of the best vacation home rentals in Windsor?

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### What are vacation rentals like in Windsor?

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