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Holiday Homes in Douglas

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Douglas holiday homes

Interior

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is €235
includes taxes & fees
30 Aug - 31 Aug
Game Room + Bar Lounge, 35 Min to Boston
Interior

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is €172
includes taxes & fees
19 Aug - 20 Aug
The Tree House at Underhill Hollow
Property grounds

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €166
includes taxes & fees
18 Aug - 19 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 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. "
United States
Mateo A.
The price is €166
includes taxes & fees
25 Aug - 26 Aug
Wizard's Roost at Underhill Hollow
3 bedrooms, desk, iron/ironing board, free WiFi

5. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
9.0 out of 10, Wonderful, (2 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is €459
includes taxes & fees
18 Aug - 19 Aug
Clifford Luxury Retreat 3BR Self Check In Home
Interior

6. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 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 "
United States
Cameron R.
The price is €226
includes taxes & fees
18 Aug - 19 Aug
Angel Sky Challenge
TV

7. By D&D Vacation Rental

By D&D Vacation Rental
Mount Pleasant
9.8 out of 10, Exceptional, (9 reviews)
"Great stay close to Mall. Close to just about anything you want to do."
United States
Tom L.
The price is €201
includes taxes & fees
1 Sept - 2 Sept
By D&D Vacation Rental
Smart TV

8. Welcome to The Adrianne!

Welcome to The Adrianne!
Elmhurst
10.0 out of 10, Exceptional, (13 reviews)
" Well, maintained home in a quiet walkable neighborhood. Great kitchen, comfy bed."
United States
Susan S.
The price is €381
includes taxes & fees
18 Aug - 19 Aug
Welcome to The Adrianne!
Private kitchen

9. Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
The price is €253
includes taxes & fees
23 Aug - 24 Aug
Charming 3-bedroom house in delightful Ashland for your getaway
Coffee/tea maker, fridge, microwave, oven

10. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 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"
United States
shawn c b.
Mohegan Sun Getaway Large Group Retreat
Coffee/tea maker, fridge, microwave, oven

11. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location"
United States
Harmony F.
The price is €431
includes taxes & fees
23 Aug - 24 Aug
Spacious 4-bedroom with four and half bathrooms
Dining

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

🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇
Federal Hill
8.8 out of 10, Excellent, (52 reviews)
"Excellent location, with parking, great communication from the host. Easy nice stay! Perfect for what I was looking for."
United States
markus
The price is €266
includes taxes & fees
19 Aug - 20 Aug
🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇
Exterior

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is €229
includes taxes & fees
18 Aug - 19 Aug
Cottage by the Castle – Downtown Spencer
Dining

14. Lovely Historic Vintage home. Remodeled inside.

Lovely Historic Vintage home. Remodeled inside.
Johnston
9.4 out of 10, Exceptional, (48 reviews)
"My host was awesome. The house was is a nice neighborhood everything we needs so close. "
United States
Tina N.
The price is €394
includes taxes & fees
15 Sept - 16 Sept
Lovely Historic Vintage home. Remodeled inside.
TV

15. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
6 Beds Home w/Game Room Perfect for Groups
Terrace/patio

16. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is €634
includes taxes & fees
30 Aug - 31 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

17. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €705
includes taxes & fees
1 Sept - 2 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Living area

18. The Quattro-Lux at Charles 4BR / 2BA with "P"+Ldry PVD. Near Providence College

The Quattro-Lux at Charles 4BR / 2BA with "P"+Ldry PVD. Near Providence College
Charles
The price is €681
includes taxes & fees
18 Aug - 19 Aug
The Quattro-Lux at Charles 4BR / 2BA with "P"+Ldry PVD. Near Providence College
Private kitchen

19. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
The price is €493
includes taxes & fees
23 Aug - 24 Aug
4-bedroom house in nice Holden with WiFi, AC
Interior

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is €794
includes taxes & fees
3 Sept - 4 Sept
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

Bally's Twin River Lincoln Casino & Hotel

Bally's Twin River Lincoln Casino & Hotel

10/10 Excellent
"Bally's is on point. Awesome hotel."
Robert 2-night trip
Posted 11 hours ago
Bally's Twin River Lincoln Casino & Hotel

Find out more about Douglas

Douglas Holiday Homes information

Number of reviews
9,772
Accommodation
124 Holiday Homes
Lowest Price
€76
Highest Price
€209