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Holiday Homes in Douglas

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Douglas holiday homes

TV

By D&D Vacation Rental

By D&D Vacation Rental
Mount Pleasant
9.8 out of 10, Exceptional, (8 reviews)
"Super nice host, had everything I needed."
United States
Jennifer M.
The price is NZ$394
includes taxes & fees
9 Aug - 10 Aug
By D&D Vacation Rental
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 NZ$336
includes taxes & fees
19 July - 20 July
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, (23 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 NZ$326
includes taxes & fees
19 July - 20 July
Wizard's Roost at Underhill Hollow
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 NZ$326
includes taxes & fees
14 July - 15 July
SteamPunk Bunk House and Intergalactic Way Station
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 NZ$508
includes taxes & fees
15 July - 16 July
Charming 3-bedroom house in delightful Ashland for your getaway
Dining

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

🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇
Federal Hill
8.8 out of 10, Excellent, (47 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 NZ$555
includes taxes & fees
15 July - 16 July
🌟Spacious + Backyard🌟50ft to Atwells & Downtown!🍝🎇
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is NZ$1,245
includes taxes & fees
19 July - 20 July
6 Beds Home w/Game Room Perfect for Groups
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 NZ$453
includes taxes & fees
14 July - 15 July
Angel Sky Challenge
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 NZ$661
includes taxes & fees
26 July - 27 July
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
The price is NZ$364
includes taxes & fees
19 July - 20 July
Cottage by the Castle – Downtown Spencer
Fridge, microwave, oven, coffee/tea maker

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.
The price is NZ$1,192
includes taxes & fees
14 July - 15 July
Mohegan Sun Getaway Large Group Retreat
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 NZ$810
includes taxes & fees
21 July - 22 July
Lovely Historic Vintage home. Remodeled inside.
Fridge, microwave, oven, stovetop

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 NZ$894
includes taxes & fees
14 July - 15 July
Spacious 4-bedroom with four and half bathrooms
Living area

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 NZ$1,361
includes taxes & fees
14 July - 15 July
The Quattro-Lux at Charles 4BR / 2BA with "P"+Ldry PVD. Near Providence College
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 NZ$1,267
includes taxes & fees
14 July - 15 July
Stunning Lakefront Escape! Book Your Dream Getaway!
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 NZ$657
includes taxes & fees
26 July - 27 July
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
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 NZ$752
includes taxes & fees
14 July - 15 July
Clifford Luxury Retreat 3BR Self Check In Home
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 NZ$906
includes taxes & fees
20 July - 21 July
Cozy 3-bedroom house in serene Worcester with fitness room and office
Private kitchen

4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
The price is NZ$963
includes taxes & fees
14 July - 15 July
4-bedroom house in nice Holden with WiFi, AC
TV, fireplace

Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (35 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is NZ$2,726
includes taxes & fees
19 July - 20 July
Sleeps 15 • Pool • Retreat
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

Embassy Suites by Hilton Boston Marlborough

Embassy Suites by Hilton Boston Marlborough

10/10 Excellent
"AMAZING! i always loving staying with Hiltons hotels! always have a great time! Spa/Pool was great! Breakfast was good, the rooms are comfortable and clean! will always choose Hilton Hotels!"
Courtney 2-night trip
Posted 7 hours ago
Embassy Suites by Hilton Boston Marlborough

Find out more about Douglas

Douglas Holiday Homes information

Number of reviews
268
Accommodation
144 Holiday Homes
Lowest Price
NZ$326
Highest Price
NZ$2,726