Dexter Holiday Rentals

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Check prices for these dates

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

Our top choices for Dexter holiday rentals

A two-story house with a wooden staircase and a balcony, two garage doors, and two ATVs parked in front.

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)
"Our 3 night stay was quiet. Even with the other unit occupied, we were very comfortable."
United States
Thayne I.
The price is NZ$273
includes taxes & fees
11 Nov - 12 Nov
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
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
The price is NZ$210
includes taxes & fees
18 Nov - 19 Nov
Rustic intown country apartment on the Moosehead trail
Living area

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, (13 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
The price is NZ$530
includes taxes & fees
11 Nov - 12 Nov
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A cabin with a porch, large windows, and a wooden deck.

4. 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
The price is NZ$426
includes taxes & fees
11 Nov - 12 Nov
Brewery Farm Retreat : Hawthorne
A spacious kitchen with wooden cabinets, a microwave, and a stove.

5. 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.
The price is NZ$255
includes taxes & fees
16 Nov - 17 Nov
The Libby House – Fast WiFi, Parking & Full Kitchen
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 traveller
The price is NZ$341
includes taxes & fees
12 Nov - 13 Nov
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A living room with a blue armchair, a beige armchair, a patterned rug, and a bookshelf with books and a plant.

7. 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.
The price is NZ$515
includes taxes & fees
20 Nov - 21 Nov
Pretty Old House in Newport
A modern log cabin interior with a gray sofa, wooden flooring, and large windows offering a view of the surrounding forest.

8. 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 NZ$426
includes taxes & fees
13 Nov - 14 Nov
Brewery Farm Retreat : Thoreau
A cabin with a deck, surrounded by trees and a lake.

9. 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.
The price is NZ$568
includes taxes & fees
11 Nov - 12 Nov
Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access
A spacious kitchen with a large island, bar stools, and modern appliances.

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.
The price is NZ$358
includes taxes & fees
17 Nov - 18 Nov
Tall Pines Retreat Escape to our charming chalet tucked away in the forest..
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

11. 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.
The price is NZ$521
includes taxes & fees
11 Nov - 12 Nov
Angel Mist Retreat Garage Apartment
A cabin with a porch, large windows, and a wooden deck.

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 NZ$426
includes taxes & fees
11 Nov - 12 Nov
Brewery Farm Cabin: Dickinson
A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

13. 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.
The price is NZ$1,012
includes taxes & fees
11 Nov - 12 Nov
Peaceful, Spacious Lodge with Golf & Sunset Views
A modern log cabin interior with a gray sofa, wooden flooring, and large windows offering a view of the surrounding forest.

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 NZ$426
includes taxes & fees
13 Nov - 14 Nov
Brewery Farm Retreat : Longfellow #7
A spacious kitchen with a granite countertop, wooden bar stools, and a ceiling fan.

15. 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
The price is NZ$414
includes taxes & fees
23 Nov - 24 Nov
Charming 2-bedroom chalet with jacuzzi WiFi and AC in Glenburn
A cozy living room with a sofa, ottoman, and dining table with chairs. There are windows with curtains, a wooden ceiling, and a view of the outdoors.

16. 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.
The price is NZ$669
includes taxes & fees
22 Nov - 23 Nov
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
IMG 7964

17. 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 NZ$974
includes taxes & fees
8 Dec - 9 Dec
Pine Tree Trail Lodge
A wooden kitchen with a large window, a black countertop, and three bar stools.

18. 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.
The price is NZ$1,174
includes taxes & fees
11 Nov - 12 Nov
Welcome to "the east Madison chapel"
A hot tub with a fire pit and chairs in a backyard with tall trees.

19. 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.
The price is NZ$1,006
includes taxes & fees
30 Nov - 1 Dec
Dog Friendly, Steps to Lake, Golf, & Theate
A dense forest with tall trees and lush green ferns.

20. Minimal & Cozy Victorian Private Room in Downtown Skowhegan

Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Skowhegan
The price is NZ$571
includes taxes & fees
17 Nov - 18 Nov
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
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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Find out more about Dexter

Everything you need to know about Dexter holiday rentals

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

Dexter holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dexter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dexter holiday rentals we have selected for you start as low as NZ$209 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dexter rentals

At Expedia, we put the best Dexter holiday 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 holiday.

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 holiday rentals in Dexter?

Yes, there are holiday rentals close to the most popular sights in Dexter, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Dexter has to offer?

Puffers Place Lodge: This highly rated holiday home rental in Dexter is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals will I find in Dexter?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Sebasticook Lake and Peaks-Kenny State Park.

What’s a holiday rental in Dexter like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dexter. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for family trips or small group gatherings.