Dexter Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Dexter vacation rentals

Property grounds

1. 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, (13 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
$264 nightly
The price is $288
Nov 16 - Nov 17
Total with taxes and fees
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A wooden deck with a table and chairs, a white house with two windows, and a door with the number 4.

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
$101 nightly
The price is $110
Nov 16 - Nov 17
Total with taxes and fees
Rustic intown country apartment on the Moosehead trail
A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

3. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (25 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
$505 nightly
The price is $551
Nov 16 - Nov 17
Total with taxes and fees
Peaceful, Spacious Lodge with Golf & Sunset Views
A patio with a table and chairs, a sliding glass door, and a yellow flowering bush.

4. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (2 reviews)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
$259 nightly
The price is $282
Nov 16 - Nov 17
Total with taxes and fees
Pretty Old House in Newport
A cabin with a porch, large windows, and a wooden deck.

5. Brewery Farm Retreat : Hawthorne

Brewery Farm Retreat : Hawthorne
Monson
10.0 out of 10, Exceptional, (6 reviews)
"The cabin was peaceful, clean, and well stocked. Lovely location, too. Close to Moosehead lake."
United States
tiffany
$221 nightly
The price is $241
Nov 16 - Nov 17
Total with taxes and fees
Brewery Farm Retreat : Hawthorne
Terrace/patio

6. 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)
"I recommend this property to anyone staying in the Pittsfield area. I’ve already suggested it to our friends who live there as great option for guests. Very clean and comfortable and a good value."
United States
Anonymous traveler
$177 nightly
The price is $193
Nov 16 - Nov 17
Total with taxes and fees
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A cabin with a covered porch, large windows, and a wooden deck.

7. 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.
$221 nightly
The price is $241
Nov 16 - Nov 17
Total with taxes and fees
Brewery Farm Retreat : Thoreau
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

8. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
United States
Ruth W.
$269 nightly
The price is $294
Nov 16 - Nov 17
Total with taxes and fees
Angel Mist Retreat Garage Apartment
A spacious kitchen with wooden cabinets, a microwave, and a stove.

9. The Libby House – Fast WiFi, Parking & Full Kitchen

The Libby House – Fast WiFi, Parking & Full Kitchen
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place!"
United States
mary jane c.
$132 nightly
The price is $144
Nov 16 - Nov 17
Total with taxes and fees
The Libby House – Fast WiFi, Parking & Full Kitchen
A modern building with a dark exterior, large windows, and a flat roof, surrounded by a snowy landscape and trees.

10. 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.
$187 nightly
The price is $204
Nov 17 - Nov 18
Total with taxes and fees
Tall Pines Retreat Escape to our charming chalet tucked away in the forest..
A cabin with a deck, surrounded by trees and a lake.

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

Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access
Monson
9.6 out of 10, Exceptional, (5 reviews)
"Super-friendly hosts! Very handy to town.Comfortable beds!!"
United States
Tim U.
$309 nightly
The price is $318
Nov 16 - Nov 17
Total with taxes and fees
Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access
IMG 7964

12. 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.
$555 nightly
The price is $559
Dec 14 - Dec 15
Total with taxes and fees
Pine Tree Trail Lodge
A hot tub in a forested area with fallen leaves.

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

Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
Glenburn
8.8 out of 10, Excellent, (3 reviews)
"Everything was perfect, If I could recommend one thing it would be free local channels on the tv"
United States
Bruce
$218 nightly
The price is $237
Nov 23 - Nov 24
Total with taxes and fees
Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
A cabin with a porch, large windows, and a wooden deck.

14. 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.
$221 nightly
The price is $241
Nov 16 - Nov 17
Total with taxes and fees
Brewery Farm Cabin: Dickinson
A lakeside seating area with Adirondack chairs and a fire pit.

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, (9 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
$338 nightly
The price is $368
Nov 22 - Nov 23
Total with taxes and fees
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
A cabin with a covered porch, large windows, and a wooden deck.

16. 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.
$221 nightly
The price is $241
Nov 16 - Nov 17
Total with taxes and fees
Brewery Farm Retreat : Longfellow #7
A dense forest with tall trees and lush green ferns.

17. Minimal & Cozy Victorian Private Room in Downtown Skowhegan

Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Skowhegan
$296 nightly
The price is $323
Nov 21 - Nov 22
Total with taxes and fees
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
A lakeside view with a floating dock and a boat.

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

Dog Friendly, Steps to Lake, Golf, & Theate
Madison
10.0 out of 10, Exceptional, (1 review)
"The house is really nice convenient local area. We would stay there again when we come into town."
United States
Al Q.
$548 nightly
The price is $597
Nov 29 - Nov 30
Total with taxes and fees
Dog Friendly, Steps to Lake, Golf, & Theate
A spacious loft with a wooden ceiling, a balcony, a staircase, and a TV mounted on the wall.

19. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (4 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.
$624 nightly
The price is $680
Nov 17 - Nov 18
Total with taxes and fees
Welcome to "the east Madison chapel"
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

A large, white two-story house with a porch and a stone wall in front.
Brewster Inn

Brewster Inn

Brewster Inn
Dexter

10/10 Excellent

The house was beautiful and had some cool history behind it.
United States
Dylan
Reviewed February 28, 2020
Brewster Inn

Find out more about Dexter

Everything you need to know about Dexter 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 Dexter 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 Dexter vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dexter vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dexter. 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 Dexter 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 $109 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 Dexter rentals

At Expedia, we put the best Dexter 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 Dexter 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 Dexter 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 Dexter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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