A calm river with a moose swimming, surrounded by dense forest and distant mountains.

Search Holiday Rentals in Shirley

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Shirley holiday rentals

A living room with two leather sofas, wooden armchairs, a patterned rug, and a wooden floor.

1. Post and beam cabin with queen size and bunk

Post and beam cabin with queen size and bunk
Shirley Mills
9.8 out of 10, Exceptional, (32 reviews)
"We thoroughly enjoyed our stay. The location, accommodations, and host (Julie), were really great! "
United States
Madeline F.
The price is £168
includes taxes & fees
16 Oct - 17 Oct
Post and beam cabin with queen size and bunk
A bunk bed with a quilted mattress featuring a wildlife print.

2. Post and beam cabin with king and bunk

Post and beam cabin with king and bunk
Shirley Mills
10.0 out of 10, Exceptional, (49 reviews)
"Another great stay at the Sunrise Cabins "
United States
Madeline F.
The price is £168
includes taxes & fees
16 Oct - 17 Oct
Post and beam cabin with king and bunk
A bathroom with a wooden floor, a white toilet, and a shower curtain depicting a mountain scene with a bear and a moose.

3. Post and beam cabin with bunk beds

Post and beam cabin with bunk beds
Shirley Mills
10.0 out of 10, Exceptional, (25 reviews)
"Nice place to stay, enjoyed the star gazing"
United States
P B.
The price is £168
includes taxes & fees
22 Oct - 23 Oct
Post and beam cabin with bunk beds
A cozy cabin interior with a fireplace, wooden floors, a sofa, a dining area, and a kitchen.

4. Private pet-friendly cabin with year round trail access

Private pet-friendly cabin with year round trail access
Shirley
The price is £391
includes taxes & fees
1 Nov - 2 Nov
Private pet-friendly cabin with year round trail access
A bedroom with a wooden bed, a dresser, a desk, and a chair.

5. Pinecone|Apartment Downtown with Fire Pit

Pinecone|Apartment Downtown with Fire Pit
Greenville
9.6 out of 10, Exceptional, (12 reviews)
"Very clean and lovely place to stay. Me and my family really enjoyed staying here. Great communication and easy check in!"
United States
Christina A.
The price is £135
includes taxes & fees
18 Oct - 19 Oct
Pinecone|Apartment Downtown with Fire Pit
A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

6. Historic barn at Moosehead Lake

Historic barn at Moosehead Lake
3.5 star property
Greenville
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect and in a great spot for all the town shops."
United States
Caitlyn
The price is £185
includes taxes & fees
18 Oct - 19 Oct
Historic barn at Moosehead Lake
Interior

7. Evergreen|Apartment Downtown with Fire Pit

Evergreen|Apartment Downtown with Fire Pit
Greenville
9.4 out of 10, Exceptional, (27 reviews)
"Very cute place! Clean. Centrally located! Would definitely go back."
United States
Louis
The price is £168
includes taxes & fees
18 Oct - 19 Oct
Evergreen|Apartment Downtown with Fire Pit
A compact living space with a dining area, a sofa, a TV mounted on the wall, and a wooden floor.

8. Downtown Greenville Spacious Apartment

Downtown Greenville Spacious Apartment
3.0 star property
Greenville
9.8 out of 10, Exceptional, (12 reviews)
"Great pre arrival comms with owner and great recommendations for dinner. The property was spotless and spacious . We used our time to find the B52 crash memorial and find the ghost trains."
United States
Ian.
The price is £162
includes taxes & fees
2 Nov - 3 Nov
Downtown Greenville Spacious Apartment
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
10.0 out of 10, Exceptional, (4 reviews)
"Super-friendly hosts! Very handy to town.Comfortable beds!!"
United States
Tim U.
The price is £263
includes taxes & fees
1 Nov - 2 Nov
Lakeshore Retreat *Waterfront*Pet Friendly*ATV Access
A wooden cabin room with a bed, a nightstand, and a chair.

10. Trails Edge*Direct ATV Access* Walk to town*Pet Friendly*Short Drive to Red Cross Beach

Trails Edge*Direct ATV Access* Walk to town*Pet Friendly*Short Drive to Red Cross Beach
Greenville
9.8 out of 10, Exceptional, (7 reviews)
"All the amenities and close to everything"
United States
Rodney S.
The price is £297
includes taxes & fees
1 Nov - 2 Nov
Trails Edge*Direct ATV Access* Walk to town*Pet Friendly*Short Drive to Red Cross Beach
A cabin with a porch, large windows, and a wooden deck.

11. 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 £174
includes taxes & fees
1 Nov - 2 Nov
Brewery Farm Cabin: Dickinson
A cabin with a porch, large windows, and a wooden deck.

12. 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 £175
includes taxes & fees
1 Nov - 2 Nov
Brewery Farm Retreat : Hawthorne
A wooden deck with a table and chairs, a white house with two windows, and a door with the number 4.

13. 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 £99
includes taxes & fees
20 Oct - 21 Oct
Rustic intown country apartment on the Moosehead trail
A forested area with a fire pit and two wooden Adirondack chairs facing a lake.

14. Cliff House* Lake View*ATV Access*Private Dock*

Cliff House* Lake View*ATV Access*Private Dock*
Greenville
10.0 out of 10, Exceptional, (6 reviews)
"Loved that we could walk onto the ice to go fishing!"
United States
Marian C.
The price is £330
includes taxes & fees
4 Nov - 5 Nov
Cliff House* Lake View*ATV Access*Private Dock*
A bedroom with a bed, a fireplace, and a deer painting on the wall.

15. Bear`s Den *ATV Access*Walk to Town/Bars/Restaurants*A/C*Pet Friendly

Bear`s Den *ATV Access*Walk to Town/Bars/Restaurants*A/C*Pet Friendly
Greenville
10.0 out of 10, Exceptional, (6 reviews)
"Clean room, steps from restaurants where we ate "
United States
Hypnophase
The price is £307
includes taxes & fees
15 Nov - 16 Nov
Bear`s Den *ATV Access*Walk to Town/Bars/Restaurants*A/C*Pet Friendly
A compact kitchen with wooden cabinets, a dining table with chairs, and a red rug.

16. ATV ACCESS/WALK TO TOWN

ATV ACCESS/WALK TO TOWN
Greenville
9.0 out of 10, Wonderful, (4 reviews)
"We had a fantastic stay here during Fly-In weekend. Walking distance from all events downtown. The accommodations were clean and perfectly met the needs of our family. Communication with property management was great! "
United States
Brianna L.
The price is £295
includes taxes & fees
10 Nov - 11 Nov
ATV ACCESS/WALK TO TOWN
A cozy living room with a dark leather couch, a dining table set with plates and glasses, and a kitchen area in the background.

17. Moose Hollow Apartment

Moose Hollow Apartment
Greenville
9.6 out of 10, Exceptional, (5 reviews)
"Great place, had everything we needed and the location was ideal!"
United States
johanna o.
The price is £326
includes taxes & fees
9 Nov - 10 Nov
Moose Hollow Apartment
A modern log cabin interior with a gray sofa, wooden flooring, and large windows offering a view of the surrounding forest.

18. 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 £181
includes taxes & fees
1 Nov - 2 Nov
Brewery Farm Retreat : Longfellow #7
A bedroom with a wooden bed, a ceiling fan, a nightstand, and a night lamp.

19. Brook Street Retreat

Brook Street Retreat
Greenville
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and had all the amenities we needed"
United States
Lynn D.
The price is £361
includes taxes & fees
19 Oct - 20 Oct
Brook Street Retreat
A modern log cabin interior with a gray sofa, wooden flooring, and large windows offering a view of the surrounding forest.

20. 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 £174
includes taxes & fees
1 Nov - 2 Nov
Brewery Farm Retreat : Thoreau
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shirley Hotel Reviews

"Andy's Place"

"Andy's Place"

10/10 Excellent
"We stayed for a long weekend on Oct. 8th through the 12th, '26. The cabin was beautiful and well stocked with everything we needed. The lake and surrounding autumn leaves were beautiful and we were able to ride about 100' down the road to the ATV trails. Greenville and Guilford in one direction and the wind towers, Harmony, and Bingham in the other. The wood stove was very nice to come back to after an all day ride."
Matthew J. 4-night trip
Posted 2 days ago
"Andy's Place"

Find out more about Shirley

Everything you need to know about Shirley 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 Shirley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Shirley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shirley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shirley. 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 Shirley 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 Shirley holiday rentals we have selected for you start as low as £168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shirley rentals

At Expedia, we put the best Shirley 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 Shirley 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 Shirley 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 Shirley. 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

Can I find a holiday rental in Shirley?

Yes, there are holiday rentals close to the most popular sights in Shirley, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Shirley has to offer?

Moosehead Hideaway (Custom-Built, Waterfront, On Moosehead Lake): This holiday home rental outside of Shirley 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. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Shirley?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Shirley stay.

What’s there to see and do in Shirley?

While exploring the area, visit family-friendly sights like Katahdin Cruises and Moosehead Marine Museum, or get outside and enjoy nature at Lake Hebron. In the wider area, you’ll find Moosehead Historical Society and Lumbermen's Museum and Big Moose Mountain.

What’s a holiday rental in Shirley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shirley. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.