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, (121)
"The place was clean and so cozy! We will be returning! "
"Andy's Place"

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

9.8 out of 10, Exceptional, (118)
"We had a lovely stay -- quite a cozy and well-appointed cabin, in an out-of-the-way spot that let us explore the area and just hunker down and enjoy the solitude, as the mood took us. Our host was very welcoming and considerate. A wonderful spot!"
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

The Cabin Skowhegan

9.8 out of 10, Exceptional, (37)
"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 Cabin Skowhegan

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

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$402
includes taxes & fees
4 Jan - 5 Jan
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

Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat

10.0 out of 10, Exceptional, (23)
"We came up for our daughter’s wedding and needed a spot to relax and reenergize between setting up, decorating, rehearsing and the big day. SugarMaple provided just that. We had my son and his girl and his best friend and his girlfriend with us and the accommodations were stellar. The view was beautiful! Thank you!! -DMB "
Sugarmaple Lakehouse; Cozy 2.6 Acre Lakefront Retreat

Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

9.6 out of 10, Exceptional, (64)
"There for project in the area .. accommodations were all as advertised .. old school camp feel with all the modern amenities .. well appointed with a local flair .. would recommend to all …"
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

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, (33)
"We had a quiet chilly weekend to relax post Thanksgiving and loved it! Hope to get to go back again. "
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!

9.4 out of 10, Exceptional, (6)
"We totally enjoyed this home and will plan to return in the future. Sleeping arrangements for 6 men was not perfect... I would highly recommend this property for a family get away! The house and location are ideal for experiencing the big woods of Maine. Hunting trip was a huge success!"
Stunning Monson Getaway on the Water!

Waterfront Lakehouse

9.8 out of 10, Exceptional, (51)
"This camp is fabulous! Happy to come back whenever we can!"
Waterfront Lakehouse

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

10.0 out of 10, Exceptional, (111)
"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

Lakefront Getaway with Kayak, Canoe and dock

10.0 out of 10, Exceptional, (3)
"Great weekend. Beautiful spot!"
Lakefront Getaway with Kayak, Canoe and dock
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$262
includes taxes & fees
6 Jan - 7 Jan
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.

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?

Four Season House - Lake Frontage with Kayaks & Dock: This holiday home rental outside of Dexter is located on a lake, and has a patio, a garden 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. Make the most of games in this rental home to help you unwind.

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 Great Moose 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.