Douglas Holiday Homes
Massachusetts
United States of America
Holiday Homes
Expedia.ie

Hotels in Douglas Holiday Rentals in Douglas Douglas Car Hire Douglas Holiday Packages

Holiday Homes in Douglas

Where to?

Dates

Travellers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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 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.

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

A room with a wooden ladder, a blue sofa, and a patterned rug.

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 €175

€175

includes taxes & fees

4 Oct - 5 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 cozy bedroom with a bed, a small table, a bookshelf, and a window with curtains.

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

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 €170

€170

includes taxes & fees

12 Oct - 13 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 room with two wicker chairs and a small round table, a large window, and a red door.

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

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 €170

€170

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

A dining area with a rectangular table, four chairs, a chandelier, and a painting on the wall.

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

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 €470

€470

includes taxes & fees

7 Oct - 8 Oct

Clifford Luxury Retreat 3BR Self Check In Home

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

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

A bedroom with a bed, desk, and computer.

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 €568

€568

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 hallway leading to a bedroom with a bed, a window with curtains, and a door marked with the number 22.

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

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

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 €231

€231

includes taxes & fees

27 Oct - 28 Oct

Angel Sky Challenge

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

A bar area with a counter, two green chairs, a refrigerator, and a neon sign.

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.

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

Game Room + Bar Lounge, 35 Min to Boston

Worcester

The price is €242

€242

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 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

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 road with a speed limit sign of 15 mph, surrounded by trees and a stone wall.

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

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 €266

€266

includes taxes & fees

13 Oct - 14 Oct

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

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

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

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

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 €445

€445

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

A cozy bedroom with a bed, a pillow with "COZY" written on it, a bottle of champagne, a glass, a small plant, and a wooden tray.

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.

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 €164

€164

includes taxes & fees

1 Nov - 2 Nov

By D&D Vacation Rental

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

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

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.

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 modern living room with a sofa, a foosball table, a TV, and a large window.

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

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 €471

€471

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 modern living room with a staircase, a sofa, a coffee table with remotes, and a ceiling fan.

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

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

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

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

Worcester

The price is €502

€502

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 €230

€230

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 microwave, a clock, and a TV mounted on the wall.

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 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.

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

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 €276

€276

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 €371

€371

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 hallway with a mural of a canal scene, wooden flooring, and a small table with a plant.

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

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.

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 €394

€394

includes taxes & fees

7 Oct - 8 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 modern kitchen with a central island, built-in appliances, and large windows offering a view of the outdoors.

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

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

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 €770

€770

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.

View all properties

Find holiday rentals that suit your style

Apartments

search for apartments

Cabins

search for cabins

Private holiday homes

search for private holiday homes

Condos

search for condos

Cottages

search for cottages

Chalets

search for chalets

Save an average of 15% on thousands of hotels when you're signed in

Top Douglas Hotel Reviews

Comfort Inn Auburn - Worcester

8/10 Good

"Good"

Frantz 1-night trip

Posted 3 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 6 hours ago

Wellsworth Hotel

Hilton Garden Inn Worcester

10/10 Excellent

"Other than the gym being to small for the size of the hotel and the parking being across the hotel everything else was fine."

Alejandro 4-night trip

Posted 12 hours ago

Hilton Garden Inn Worcester

Hampton Inn Pawtucket

10/10 Excellent

"Amazing stay"

Brenda 2-night trip

Posted 14 hours 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 22 hours 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 3 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 4 days ago

Sonesta Select Boston Milford

Find out more about Douglas

Douglas Holiday Homes information

Number of reviews	294
Accommodation	147 Holiday Homes
Lowest Price	€164
Highest Price	€770

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