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Holiday Homes in Douglas

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Douglas holiday homes

Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is AU$280
includes taxes & fees
3 Aug - 4 Aug
The Tree House at Underhill Hollow
Exterior

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 AU$271
includes taxes & fees
23 July - 24 July
Wizard's Roost at Underhill Hollow
Property grounds

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)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is AU$542
includes taxes & fees
26 July - 27 July
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$271
includes taxes & fees
3 Aug - 4 Aug
SteamPunk Bunk House and Intergalactic Way Station
3 bedrooms, desk, iron/ironing board, free WiFi

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is AU$644
includes taxes & fees
23 July - 24 July
Clifford Luxury Retreat 3BR Self Check In Home
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is AU$493
includes taxes & fees
17 Aug - 18 Aug
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Coffee/tea maker, fridge, microwave, oven

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"Perfect location"
United States
Harmony F.
The price is AU$723
includes taxes & fees
28 July - 29 July
Spacious 4-bedroom with four and half bathrooms
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (26 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is AU$1,047
includes taxes & fees
23 July - 24 July
Stunning Lakefront Escape! Book Your Dream Getaway!
Property grounds

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)
"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."
United States
Kyle C.
The price is AU$926
includes taxes & fees
26 July - 27 July
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"The only thing missing was a BBQ"
United States
Charmen B.
The price is AU$738
includes taxes & fees
23 July - 24 July
Cozy 3-bedroom house in serene Worcester with fitness room and office
TV

By D&D Vacation Rental

By D&D Vacation Rental
Mount Pleasant
9.8 out of 10, Exceptional, (9 reviews)
"Super nice host, had everything I needed."
United States
Jennifer M.
The price is AU$297
includes taxes & fees
23 July - 24 July
By D&D Vacation Rental
Private kitchen

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 AU$418
includes taxes & fees
26 July - 27 July
Charming 3-bedroom house in delightful Ashland for your getaway
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (2 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AU$370
includes taxes & fees
4 Aug - 5 Aug
Cottage by the Castle – Downtown Spencer
Interior

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 AU$370
includes taxes & fees
23 July - 24 July
Angel Sky Challenge
Dining

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 AU$1,093
includes taxes & fees
23 July - 24 July
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Smart TV

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 AU$616
includes taxes & fees
6 Aug - 7 Aug
Welcome to The Adrianne!
Dining

Lovely Historic Vintage home. Remodeled inside.

Lovely Historic Vintage home. Remodeled inside.
Johnston
9.4 out of 10, Exceptional, (46 reviews)
"My host was awesome. The house was is a nice neighborhood everything we needs so close. "
United States
Tina N.
The price is AU$661
includes taxes & fees
28 July - 29 July
Lovely Historic Vintage home. Remodeled inside.
Coffee/tea maker, fridge, microwave, oven

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
Private kitchen

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 AU$801
includes taxes & fees
23 July - 24 July
4-bedroom house in nice Holden with WiFi, AC
Dining

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

🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇
Federal Hill
8.8 out of 10, Excellent, (48 reviews)
"A nice spacious place on a quiet side street just a very short walk to downtown. A great location if you want to get out and explore. The host was quick to respond with any questions. I will definitely look for this location if I plan another trip. Thanks - Bill"
United States
Bill R.
The price is AU$461
includes taxes & fees
30 July - 31 July
🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇
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

Renaissance Providence Downtown Hotel

Renaissance Providence Downtown Hotel

10/10 Excellent
"One night stay. Clean room, great service ,and great location"
Jeffrey 1-night trip
Posted 15 hours ago
Renaissance Providence Downtown Hotel

Find out more about Douglas

Douglas Holiday Homes information

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