Book Holiday Homes in Dexter

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Dexter

Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly

Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly

Canaan
With a stay at this vacation home in Canaan, you'll be within a 15-minute drive of Eaton Mountain and JW Parks Golf Course.
Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

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

Madison
Located in Madison, this vacation home is on a lake, a 4-minute drive from Inland Hospital and 8 minutes from Skowhegan State Fairgrounds.
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Modern Cornville Ranch

Modern Cornville Ranch

Cornville
When you stay at this vacation home in Skowhegan, you'll be 14 minutes by car from Kennebec River.
Modern Cornville Ranch
Save an average of 15% on thousands of hotels when you're signed in
Charming, lakefront dog-friendly home with a firepit, dock, & fast WiFi

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

Monson
Located in Monson, this vacation home is on the waterfront, within a 15-minute drive of Lake Hebron and Abbot Evangelical Free Church.
Charming, lakefront dog-friendly home with a firepit, dock, & fast WiFi
Waterfront Lakehouse

Waterfront Lakehouse

Stetson
With a stay at this vacation home in Stetson, you'll be on the waterfront, and 19.1 mi (30.7 km) from Maine Savings Amphitheater and 25.8 mi (41.4 km) from Cross ...
Waterfront Lakehouse
Four Season House - Lake Frontage with Kayaks & Dock

Four Season House - Lake Frontage with Kayaks & Dock

Sebec
When you stay at this vacation home in Sebec, you'll be on the waterfront and 9 minutes by car from Pleasant River.
Four Season House - Lake Frontage with Kayaks & Dock
The Great Moose in Stunning Maine  Swim, Fish & Kayak

The Great Moose in Stunning Maine Swim, Fish & Kayak

Hartland
You'll be centrally located in Hartland with a stay at this vacation home, and 11 minutes by foot from Great Moose Lake.
The Great Moose in Stunning Maine Swim, Fish & Kayak
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
Located in Sangerville, this vacation home is in a rural location, within a 15-minute drive of Lake Wassookeag and Lowe's Covered Bridge.
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Two Home Retreat Meant for Big Family Memories

Two Home Retreat Meant for Big Family Memories

Parkman
Located in Guilford, this vacation home is on the waterfront, within a 15-minute drive of Lowe's Covered Bridge and Abbot Evangelical Free Church.
Two Home Retreat Meant for Big Family Memories
Don't see what you're looking for?
See all available properties in Dexter
View all properties
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.

Dexter Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Dexter vacation homes are the perfect way for you to wing it.

Holiday houses in Dexter let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Dexter in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Dexter adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Dexter with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Dexter vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Dexter Holiday Homes essential information

Accommodation
52 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly, Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach, Modern Cornville Ranch, Charming, lakefront dog-friendly home with a firepit, dock, & fast WiFi, Waterfront Lakehouse, Four Season House - Lake Frontage with Kayaks & Dock, The Great Moose in Stunning Maine Swim, Fish & Kayak, Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard, Two Home Retreat Meant for Big Family Memories

Top trending hotels in Dexter

Brewster Inn

Brewster Inn

3.5 out of 5
37 Zions Hill Road, Dexter, ME
Fully refundableReserve now, pay when you stay
With a stay at Brewster Inn in Dexter, you'll be 13.8 mi (22.3 km) from Lowe's Covered Bridge and 19.4 mi (31.3 km) from Peaks-Kenny State Park.
Brewster Inn
Taylor Edes Inn

Taylor Edes Inn

3 out of 5
20 High Street, Dexter, ME
Fully refundable
Located in Dexter, Taylor Edes Inn is within a 15-minute drive of Lake Wassookeag and Sebasticook Lake.
Taylor Edes Inn
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

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

Dexter
When you stay at this cabin in Dexter, you'll be 14 minutes by foot from Lake Wassookeag.
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
Save an average of 15% on thousands of hotels when you're signed in
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly

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

Dexter
When you stay at this cabin in Dexter, you'll be on the waterfront and steps from Lake Wassookeag.
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly
Don't see what you're looking for?
See all available properties in Dexter
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.