A forest with autumn foliage, a winding road, and distant mountains.

Dexter Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Dexter vacation rentals

Exterior

1. New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville

New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Sangerville
7.2 out of 10, Good, (5 reviews)
"Cozy room, very nice bathroom and shower, beautiful setti ng and very accomadating and available host"
United States
Judith L.
The price is AED 327
AED 637 total
includes taxes & fees
29 Sep - 30 Sep
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Outdoor dining

2. Rustic intown country apartment on the Moosehead trail

Rustic intown country apartment on the Moosehead trail
Sangerville
9.6 out of 10, Exceptional, (48 reviews)
"The place was a very nice place to stay"
United States
Ruth
The price is AED 244
AED 466 total
includes taxes & fees
1 Oct - 2 Oct
Rustic intown country apartment on the Moosehead trail
Smart TV, fireplace, DVD player, books

3. Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Sangerville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Outdoor dining

4. Gorgeous 2-bedroom cottage with AC in charming Stetson

Gorgeous 2-bedroom cottage with AC in charming Stetson
Stetson
10.0 out of 10, Exceptional, (21 reviews)
"Very nice. Will stay there again"
United States
Andy O.
The price is AED 606
AED 741 total
includes taxes & fees
29 Sep - 30 Sep
Gorgeous 2-bedroom cottage with AC in charming Stetson
Exterior

5. Brewery Farm Retreat : Hawthorne

Brewery Farm Retreat : Hawthorne
Monson
10.0 out of 10, Exceptional, (5 reviews)
"The cabin was very nice very quiet just what we were looking for"
United States
JonPaul B.
The price is AED 536
AED 925 total
includes taxes & fees
1 Oct - 2 Oct
Brewery Farm Retreat : Hawthorne
Smart TV, fireplace, books

6. Brewery Farm Retreat : Thoreau

Brewery Farm Retreat : Thoreau
Monson
9.6 out of 10, Exceptional, (5 reviews)
"We enjoyed out stay with our two pups in the Thoreau cabin. It was quiet and enjoyable. We will be back!"
United States
Alyssa M.
The price is AED 507
AED 893 total
includes taxes & fees
29 Sep - 30 Sep
Brewery Farm Retreat : Thoreau
Terrace/patio

7. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Pittsfield
9.8 out of 10, Exceptional, (10 reviews)
"Great host great stay"
United States
thomas v.
The price is AED 437
AED 817 total
includes taxes & fees
29 Sep - 30 Sep
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
DVD player, books, offices

8. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (1 review)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is AED 477
AED 1,081 total
includes taxes & fees
29 Sep - 30 Sep
Pretty Old House in Newport
Terrace/patio

9. Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access

Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access
Monson
10.0 out of 10, Exceptional, (4 reviews)
"Super-friendly hosts! Very handy to town.Comfortable beds!!"
United States
Tim U.
The price is AED 303
AED 1,181 total
includes taxes & fees
29 Sep - 30 Sep
Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access
Exterior

10. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is AED 516
AED 1,083 total
includes taxes & fees
29 Sep - 30 Sep
Angel Mist Retreat Garage Apartment
Exterior

11. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (24 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is AED 1,055
AED 2,074 total
includes taxes & fees
29 Sep - 30 Sep
Peaceful, Spacious Lodge with Golf & Sunset Views
Exterior

12. Brewery Farm Cabin: Dickinson

Brewery Farm Cabin: Dickinson
Monson
9.8 out of 10, Exceptional, (7 reviews)
"This is a magical place! Super new, clean, relaxing and has everything you need. The location is quiet and serene. The bed is so comfortable. Nice linens, equipped kitchen and comfortable living area. I can’t wait to come back!"
United States
Nancy G.
The price is AED 522
AED 909 total
includes taxes & fees
29 Sep - 30 Sep
Brewery Farm Cabin: Dickinson
Private kitchen

13. Tall Pines Retreat Escape to our charming chalet tucked away in the forest..

Tall Pines Retreat Escape to our charming chalet tucked away in the forest..
Glenburn
10.0 out of 10, Exceptional, (4 reviews)
"The stay was great! My boyfriend and i planned an ice fishing trip and this place was perfect! Gorgeous, clean and the property owner was super responsive! We will definitely book there again!"
United States
Briana H.
The price is AED 857
AED 1,014 total
includes taxes & fees
27 Oct - 28 Oct
Tall Pines Retreat Escape to our charming chalet tucked away in the forest..
Smart TV, fireplace

14. Brewery Farm Retreat : Longfellow #7

Brewery Farm Retreat : Longfellow #7
Monson
10.0 out of 10, Exceptional, (6 reviews)
"Great spot to enjoy some local craft beer in the peace and quiet!"
United States
Jacob R.
The price is AED 540
AED 929 total
includes taxes & fees
20 Oct - 21 Oct
Brewery Farm Retreat : Longfellow #7
Smart TV, books

15. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
9.8 out of 10, Exceptional, (8 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is AED 617
AED 1,449 total
includes taxes & fees
7 Oct - 8 Oct
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Interior

16. Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn

Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
Glenburn
8.0 out of 10, Very good, (2 reviews)
"Everything was perfect, If I could recommend one thing it would be free local channels on the tv"
United States
Bruce
The price is AED 1,061
AED 1,248 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
Interior

17. Dog Friendly, Steps to Lake, Golf, & Theate

Dog Friendly, Steps to Lake, Golf, & Theate
Madison
"The house is really nice convenient local area. We would stay there again when we come into town."
United States
Al Q.
The price is AED 767
AED 1,849 total
includes taxes & fees
29 Sep - 30 Sep
Dog Friendly, Steps to Lake, Golf, & Theate
Private kitchen

18. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (3 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
The price is AED 1,469
AED 2,486 total
includes taxes & fees
29 Sep - 30 Sep
Welcome to "the east Madison chapel"
Property grounds

19. Minimal & Cozy Victorian Private Room in Downtown Skowhegan

Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Skowhegan
The price is AED 735
AED 1,181 total
includes taxes & fees
4 Oct - 5 Oct
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Fridge, microwave, oven, stovetop

20. Pine Tree Trail Lodge

Pine Tree Trail Lodge
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is AED 5,090
AED 6,077 total
includes taxes & fees
27 Oct - 28 Oct
Pine Tree Trail Lodge
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 Dexter Hotel Reviews

Canaan Motel

Canaan Motel

10/10 Excellent
"My wife and I stayed here while attending the Common Ground Fair. As far as we could tell, Neal alone orchestrated and performed all duties. He was very friendly and helpful. Our room was nice & clean and well kept. Comfortable bed! It’s a motel, so don’t expect frills. Nice grounds in back, with a seasonal pool. Trails into the woods. Quiet. Great stay. Will stay again. Thanks Neal!"
Michael 2-night trip
Posted 1 hour ago
Canaan Motel

Frequently asked questions

Are there vacation rentals in Dexter?

Yes, we offer vacation rentals close to well known local attractions in Dexter, or you can select a more secluded option if you want a relaxing place to stay. Dexter is known for its shopping and gardens. Make sure you have time to check out the entertainment choices and restaurants during your trip.

What are some of the best vacation rentals that Dexter has to offer?

Puffers Place Lodge: This highly rated vacation home rental in Dexter is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals will I find in Dexter?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Dexter stay.

What’s there to see and do in Dexter?

While exploring the area, visit family-friendly sights like Piscatiquis County Ice Arena, or get outside and enjoy nature at Lake Wassookeag. In the larger area, you’ll find Sebasticook Lake and Peaks-Kenny State Park.

What’s a vacation rental in Dexter like?

Vacation rentals are private properties where you can stay for a long or short time in Dexter. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.