Dexter Holiday Rentals

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Holiday Rentals in Dexter

Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly

10.0 out of 10, Exceptional, (13)
"Beautiful house and quiet location on the water. It’s our second time here and looking forward to coming back."
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly

Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

10.0 out of 10, Exceptional, (10)
"We had a very relaxing time. The place had everything we needed. Atmosphere in the house was perfect. Just plain relaxing. Thank you. "
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

"Andy's Place"

10.0 out of 10, Exceptional, (118)
"We had an awesome stay at Andy's Place. Kitchen was fully stocked with the essentials to cook. Nice location and excellent spot for boating fan."
"Andy's Place"

The Cabin Skowhegan

9.8 out of 10, Exceptional, (36)
"Larry hosted us for a week with our dogs while we were on a house-hunting expedition. Larry was a perfect host; very attentive but allowed us our space. The Cabin is very cozy and while there is no kitchen sink, the property details disclose this so we were prepared. It was a wonderful stay!"
The price is AU$290
includes taxes & fees
1 Dec - 2 Dec
The Cabin Skowhegan

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

9.8 out of 10, Exceptional, (117)
"It was an absolutely beautiful cabin hard to get to so the directions should be changed because it takes through the back side in order to get into the location and then you end up having to turn around because you end up in a corn field in the middle of the night and that's a little rugged no TVs in any of the rooms. Other than that our stay was amazing. Very clean everything equipped inside. You just had to get your own food and stuff. Other than that we enjoyed our stay and hope to be back"
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

9.8 out of 10, Exceptional, (110)
"We totally loved our stay. We are talking about our next stay. "
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

The Cabbage on Olive Street, overlooking Hayden Brook

9.0 out of 10, Wonderful, (11)
"If you, dear reader, and I have anything in common, then you're reading this at 1am after a long work day and you've reached this listing by googling "places to stay in Maine under $100." You're also probably saying to yourself "What a quaint little cabin in the heart of Stephen King country! I wonder if anything Stephen King-related would happen to me if I stayed there?" Dear reader, let me put your fears to rest: book the dang cabin!!! I went here on my first solo vacation and could not have...
The Cabbage on Olive Street, overlooking Hayden Brook

Charming, lakefront dog-friendly home with a firepit, dock, & fast WiFi

8.0 out of 10, Very good, (2)
Charming, lakefront dog-friendly home with a firepit, dock, & fast WiFi

Wonderful Lakefront Gem W/ Free WiFi, Dock, Private Beach, Kayaks, Canoe & More

9.4 out of 10, Exceptional, (16)
"Our family stayed during the 2024 Eclipse, and we enjoyed an amazing experience in a beautiful location! Pros: excellent location right on the lake, well-stocked kitchen with relatively sharp knives (unusual for a rental!), great communication with the local agent, easy check-in and check-out. It was actually a bigger space than it looked like in the photos online. Cons: The plumbing is a little funky - the sink and downstairs toilet gurgles when you flush the upstairs toilet. The downstairs...
Wonderful Lakefront Gem W/ Free WiFi, Dock, Private Beach, Kayaks, Canoe & More

Cozy cabin with direct atv/snowmobile trail access

9.8 out of 10, Exceptional, (26)
"beautiful place to stay "
Cozy cabin with direct atv/snowmobile trail access

Rustic intown country apartment on the Moosehead trail

9.8 out of 10, Exceptional, (37)
"Our place wasn't great. The hosts were wonderful. Would stay again!"
The price is AU$150
includes taxes & fees
9 Dec - 10 Dec
Rustic intown country apartment on the Moosehead trail

Wicked Cute Cabin along the Piscataquis River

9.6 out of 10, Exceptional, (7)
"Adorable little cabin, perfect size for an overnight getaway with my sister. "
The price is AU$383
includes taxes & fees
24 Nov - 25 Nov
Wicked Cute Cabin along the Piscataquis River

Enchanting dog-friendly cottage with full kitchen, fast WiFi, & nearby creek

10.0 out of 10, Exceptional, (2)
"This place was very cozy & nicely situated. We’d love to come back in the future! "
Enchanting dog-friendly cottage with full kitchen, fast WiFi, & nearby creek

Gorgeous Yr-Round Lake House w/2 Master BRs & Loft

10.0 out of 10, Exceptional, (19)
"Such a peaceful space with all the perks. Clean, comfortable, spacious. Everything included is high quality- beds, sheets, towels, kitchen appliances and more. Great views of sun and moon rise. Owners very responsive. Absolutely perfect!"
Gorgeous Yr-Round Lake House w/2 Master BRs & Loft

Waterfront Sebec Lake Home w/ Yard + Fire Pit

10.0 out of 10, Exceptional, (10)
"Place was as advertised, clean and well appointed. Owner was responsive. We would definately rent from him again."
Waterfront Sebec Lake Home w/ Yard + Fire Pit

Central Maine Waterfront

9.6 out of 10, Exceptional, (5)
"This property was full off character with barn wood lined walls and cute fixtures. John was incredibly hospitable and made us feel like family. "
Central Maine Waterfront

Cozy cabin with 200’ of waterfront on Whites Pond

9.6 out of 10, Exceptional, (31)
"The cabin on Whites pond is a very nice cozy cabin on a beautiful pond. It was clean and very comfortable. You can tell it is a cabin that family enjoys. Loved the Indian looking out over the water. Truly a lovely cabin. So sorry about the floor. I am glad that the charge was applied for the repair. "
Cozy cabin with 200’ of waterfront on Whites Pond

Four Season House - Lake Frontage with Kayaks & Dock

9.8 out of 10, Exceptional, (54)
"This is a wonderful cabin in a secluded and quiet spot. The hosts were wonderful, responsive and helpful throughout the process. The cabin was set up with Roku TV and games and puzzles. Beds were comfortable. The overall experience was relaxing and perfect for some time away."
Four Season House - Lake Frontage with Kayaks & Dock

Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

9.8 out of 10, Exceptional, (149)
"Loved this place and so did our dogs. Definately want to come back. Amazing huge wood fireplace and lots of land right out the back door to explore and throw the frisbee. It would be a great place for kids too. So quiet! No airplane noise even! No cars or neighbor noises. Clean, very comfy beds, well stocked kitchen and linens and even a washer/dryer. Also decent water pressure and a combo hand/regular shower head came in handy. Huge too with multiple beds. Two bedrooms with pocket doors that...
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

Stunning Monson Getaway on the Water!

9.2 out of 10, Wonderful, (5)
"The property was clean and accurately represented in the listing. The water in the pond was very clean and pleasant for swimming. Lots of space for 6 people, well stocked with towels etc. and some very nice kayaks with paddles in good shape. The pond and neighborhood are very quiet. Fireflies all over & very dark skies for stargazing. I would say that the only two things I would have liked to have known in advance are 1) the internet is quite slow, zero cell svc, we did manage to stream Netflix...
Stunning Monson Getaway on the Water!
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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Other types of properties in Dexter you may be interested in

Taylor Edes Inn

3.0 star property
9.6 out of 10, Exceptional, (265)
"Everything I needed, comfortable bed"
The price is AU$200
includes taxes & fees
25 Nov - 26 Nov
Taylor Edes Inn

Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly

10.0 out of 10, Exceptional, (13)
"Beautiful house and quiet location on the water. It’s our second time here and looking forward to coming back."
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly

Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

10.0 out of 10, Exceptional, (10)
"We had a very relaxing time. The place had everything we needed. Atmosphere in the house was perfect. Just plain relaxing. Thank you. "
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

New, stunning 3-bedroom, 5 acre home! Direct access to snowmobile & ATV trails: This holiday home rental outside of Dexter is located near skiing, and offers a selection of games, laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Dexter?

With 4 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 Lowe's Covered Bridge and Sebasticook Lake.

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.