Douglas Holiday Homes
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Our top choices for Douglas holiday homes

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

A two-story wooden house with a deck and a staircase.

A bedroom with a sloped ceiling, wooden walls, and two skylights.

A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson

9.4 out of 10, Exceptional, (42 reviews)

9.4/10

Exceptional

(42 reviews)

"Great space, lots of fun."

Douglas C.

The price is £149

£149

includes taxes & fees

5 Oct - 6 Oct

The Tree House at Underhill Hollow

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

A compact room with a bed, a small table with a chessboard, a bathroom, and a window with curtains.

A room with two beds, a red door with a dragon emblem, and colorful wall decorations.

A cozy bedroom with a bed, a small table, a bookshelf, and a window with curtains.

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow

North Grosvenordale

9.6 out of 10, Exceptional, (26 reviews)

9.6/10

Exceptional

(26 reviews)

"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "

Mateo A.

The price is £145

£145

includes taxes & fees

8 Oct - 9 Oct

Wizard's Roost at Underhill Hollow

Two front-loading washing machines in a laundry room with a wooden floor and a wall-mounted light fixture.

A living room with a sofa, armchair, and a television.

A two-story house with a red door, white windows, and a wooden staircase.

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station

Thompson

10.0 out of 10, Exceptional, (18 reviews)

10/10

Exceptional

(18 reviews)

"Enjoyed our stay. Loved being out in the countryside "

Pauline S.

The price is £145

£145

includes taxes & fees

4 Oct - 5 Oct

SteamPunk Bunk House and Intergalactic Way Station

A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

A room with a wooden ceiling, a ceiling fan, a sectional sofa, a coffee table, and a patterned rug.

A two-story building with a garage, a balcony, and a flag.

A living room with a television, a sofa, a coffee table, a globe, and a fireplace.

4. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home

Northbridge

8.6 out of 10, Excellent, (7 reviews)

8.6/10

Excellent

(7 reviews)

The price is £402

£402

includes taxes & fees

5 Oct - 6 Oct

Clifford Luxury Retreat 3BR Self Check In Home

A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

A bedroom with a bed, desk, and computer.

A window with a 'Cheers' sign, a hanging light fixture, and a view of a yard with trees and a fence.

5. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Webster

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."

Rachele T.

The price is £484

£484

includes taxes & fees

14 Oct - 15 Oct

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

A modern bedroom with a bed, a mirror, an air conditioning unit, a TV, and a thermostat.

A two-story house with a central entrance, a brick foundation, and a large front yard.

A modern hallway with a black and white patterned carpet, a staircase with a granite handrail, and a door with a black frame.

6. Angel Sky Challenge

Angel Sky Challenge

Worcester

2.0 out of 10, (1 review)

2.0/10

(1 review)

"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "

Cameron R.

The price is £201

£201

includes taxes & fees

4 Oct - 5 Oct

Angel Sky Challenge

A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

A laundry room with a washing machine, a dryer, and visible plumbing.

A covered deck with outdoor furniture, a grill, and a sliding glass door leading to a bedroom.

A kitchen with wooden cabinets, a black refrigerator, a microwave, and a granite countertop.

7. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston

Worcester

The price is £206

£206

includes taxes & fees

4 Oct - 5 Oct

Game Room + Bar Lounge, 35 Min to Boston

A living room with a wooden staircase, a gray sectional sofa, a colorful rug, and a ceiling fan.

A room with a treadmill, exercise equipment, a desk, and a potted plant.

A neatly made bed with white linens and a textured throw pillow, a bedside lamp, a small basket with water bottles, and a framed picture on the wall.

A dining area with a wooden table, chairs, and a vase with flowers.

8. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Worcester

The price is £374

£374

includes taxes & fees

14 Oct - 15 Oct

Spacious 5-bedroom home with three full bathrooms in charming Worcester location

A living room with a sofa, a clock, a floor lamp, and a rug.

A compact kitchen with white cabinets, a black countertop, a stainless steel stove, a coffee maker, a microwave, and a sink.

A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

A living room with a flat-screen TV mounted above a white brick fireplace, surrounded by bookshelves and a coffee table with a vase.

9. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury

9.4 out of 10, Exceptional, (55 reviews)

9.4/10

Exceptional

(55 reviews)

"Amazing host and fabulous spacious property. "

Kelly L.

The price is £227

£227

includes taxes & fees

14 Oct - 15 Oct

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

A dining area with a wooden table and chairs, a central decorative piece, and large windows with curtains.

A compact kitchen with a stainless steel refrigerator, a microwave, and a built-in oven. It features white cabinetry, a wooden floor, and a window providing a view of the outside.

A hallway with wooden flooring, a black console table, a staircase with white railings, and a door leading to a kitchen area.

10. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester

9.8 out of 10, Exceptional, (22 reviews)

9.8/10

Exceptional

(22 reviews)

"Perfect location"

Harmony F.

The price is £379

£379

includes taxes & fees

4 Oct - 5 Oct

Spacious 4-bedroom with four and half bathrooms

A loft-style room with a wooden staircase, a sofa, a TV, and a 'Take a hike' sign.

A black wrought iron gate with intricate designs and a coat of arms above it, flanked by two brick pillars with decorative elements.

A modern kitchen with a white refrigerator, a microwave, and a coffee machine. There are three bar stools and a wooden table with a bowl of decorative items.

A marina with boats docked, a bridge in the background, and a city skyline.

11. By D&D Vacation Rental

By D&D Vacation Rental

Mount Pleasant

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Great stay close to Mall. Close to just about anything you want to do."

Tom L.

The price is £139

£139

includes taxes & fees

1 Nov - 2 Nov

By D&D Vacation Rental

A covered porch with a cushioned seating area, a small table, and a view of a residential neighborhood.

A two-story house with a porch and a stone wall in front.

12. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Webster

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."

Kyle C.

The price is £666

£666

includes taxes & fees

14 Oct - 15 Oct

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

A living room with a sofa, a foosball table, a TV, and a fireplace.

A bedroom with two beds, a nightstand, a window with curtains, and a framed picture on the wall.

A dining area with a wooden table, chairs, a ceiling fan, a clock, and a cabinet with plants.

13. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat

Killingly

7.4 out of 10, Good, (3 reviews)

7.4/10

Good

(3 reviews)

"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"

shawn c b.

The price is £401

£401

includes taxes & fees

4 Oct - 5 Oct

Mohegan Sun Getaway Large Group Retreat

A two-story residential building with a front porch, a satellite dish, and a small front yard.

A bedroom with a bed, a dresser, a ceiling fan, and a window with curtains.

A compact kitchen with a microwave, oven, and a small island with a sink.

A residential property with a grassy yard, a tree, and a house in the background.

14. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Worcester

The price is £445

£445

includes taxes & fees

13 Oct - 14 Oct

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

The Cottage is nestled next to the historic Sagendorph Mansion.

15. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer

Spencer

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"

Fabiola

The price is £196

£196

includes taxes & fees

12 Oct - 13 Oct

Cottage by the Castle – Downtown Spencer

A modern interior with a kitchen, dining area, and living space.

A modern hotel room with a large bed, a desk, a chair, a TV, and a window with a view of buildings.

A wooden table and chairs set in a grassy outdoor area with a grill.

A modern kitchen with white cabinetry, a stainless steel stove, a microwave, and a clock above the sink.

16. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups

Killingly

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Edgar was very responsive and easy to work with. The unit was very clean and well kept. I would definitely stay there again."

debra l.

6 Beds Home w/Game Room Perfect for Groups

A dining table set with plates, cutlery, and a decorative wooden link.

A kitchen with wooden cabinets, a stainless steel microwave, a gas stove, and a sink.

A bedroom with a bed, a dresser, and a mirror.

A patio with a table and chairs, surrounded by a house with a covered porch and pine trees.

17. 🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇

🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇

Federal Hill

8.8 out of 10, Excellent, (53 reviews)

8.8/10

Excellent

(53 reviews)

"Great location with many dining options."

Ric S.

The price is £233

£233

includes taxes & fees

5 Oct - 6 Oct

🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇

A modern kitchen with white brick walls, a dining area with a wooden table and benches, and a TV mounted on the wall.

A bedroom with two beds, a nautical-themed bedspread, a chandelier, and a painting of sailboats.

A window with a view of a snow-covered landscape, including trees and a path.

A campfire in a wooded area with trees and a distant house.

18. Lovely Historic Vintage home. Remodeled inside.

Lovely Historic Vintage home. Remodeled inside.

Johnston

9.4 out of 10, Exceptional, (51 reviews)

9.4/10

Exceptional

(51 reviews)

"My host was awesome. The house was is a nice neighborhood everything we needs so close. "

Tina N.

The price is £315

£315

includes taxes & fees

2 Nov - 3 Nov

Lovely Historic Vintage home. Remodeled inside.

A modern living room with a blue sofa, a glass coffee table, a white entertainment unit, and a large flat-screen TV.

A dining area with a glass table and wicker chairs, a hanging light fixture, and a wall mural.

A neatly made bed with a white comforter and a beige throw blanket, a bedside table with a tray holding a small plant and a book, and a large mirror on the wall.

A kitchen with wooden cabinets, a white countertop, and a vase with white flowers on a white stand.

19. Welcome to The Adrianne!

Welcome to The Adrianne!

Elmhurst

9.6 out of 10, Exceptional, (17 reviews)

9.6/10

Exceptional

(17 reviews)

" Well, maintained home in a quiet walkable neighborhood. Great kitchen, comfy bed."

Susan S.

The price is £320

£320

includes taxes & fees

22 Oct - 23 Oct

Welcome to The Adrianne!

A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

A boat interior with a large window overlooking a lake, a tree trunk, and a seating area with cushions.

A lakeside house with a dock, a covered boat launch, and a well-maintained lawn.

A modern kitchen with a central island, built-in appliances, and large windows offering a view of the outdoors.

20. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge

9.6 out of 10, Exceptional, (24 reviews)

9.6/10

Exceptional

(24 reviews)

"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."

Christian C.

The price is £656

£656

includes taxes & fees

4 Oct - 5 Oct

Lake House in Sturbridge w/All the Views!

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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Top Douglas Hotel Reviews

Comfort Inn Auburn - Worcester

8/10 Good

"Good"

Frantz 1-night trip

Posted 13 hours ago

Comfort Inn Auburn - Worcester

Wellsworth Hotel

10/10 Excellent

"This is our 6th time staying here, we love it. Its our Home away from Home❤️ The amenities are so nice its such a relaxing atmosphere and always a clean hotel stay every time. We are so grateful for this place!"

Melissa 2-night trip

Posted 16 hours ago

Wellsworth Hotel

Hampton Inn Pawtucket

10/10 Excellent

"Amazing stay"

Brenda 2-night trip

Posted 1 day ago

Hampton Inn Pawtucket

Providence Marriott Downtown

10/10 Excellent

"Your staff allowed me to give this hotel the highest rating. They responded quickly to every request. Am particularly appreciative of their response to my need for blankets when the dropped overnight."

Cecille 3-night trip

Posted 1 day ago

Providence Marriott Downtown

Bally's Twin River Lincoln Casino & Hotel

10/10 Excellent

"We had a great stay! Thank you!"

Jay 1-night trip

Posted 2 days ago

Bally's Twin River Lincoln Casino & Hotel

Courtyard by Marriott Boston Marlborough

10/10 Excellent

"Nice place. Perfect"

Kathleen 1-night trip

Posted 4 days ago

Courtyard by Marriott Boston Marlborough

Sonesta Select Boston Milford

10/10 Excellent

"Room was very cleaning staff was great 👍"

CINDY 2-night trip

Posted 5 days ago

Sonesta Select Boston Milford

Find out more about Douglas

Douglas Holiday Homes information

Number of reviews	294
Accommodation	149 Holiday Homes
Lowest Price	£139
Highest Price	£666

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Douglas on Expedia.com

Search Holiday Homes in Douglas

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Douglas holiday homes

1. The Tree House at Underhill Hollow

2. Wizard's Roost at Underhill Hollow

3. SteamPunk Bunk House and Intergalactic Way Station

4. Clifford Luxury Retreat 3BR Self Check In Home

5. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

6. Angel Sky Challenge

7. Game Room + Bar Lounge, 35 Min to Boston

8. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

9. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

10. Spacious 4-bedroom with four and half bathrooms

11. By D&D Vacation Rental

12. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

13. Mohegan Sun Getaway Large Group Retreat

14. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

15. Cottage by the Castle – Downtown Spencer

16. 6 Beds Home w/Game Room Perfect for Groups

17. 🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇

18. Lovely Historic Vintage home. Remodeled inside.

19. Welcome to The Adrianne!

20. Lake House in Sturbridge w/All the Views!

Find holiday rentals that suit your style

Top Douglas Hotel Reviews

Comfort Inn Auburn - Worcester

Find out more about Douglas

Douglas Holiday Homes information

Explore a world of travel with Expedia