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Douglas Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Douglas vacation rentals

3 bedrooms, desk, iron/ironing board, WiFi (free)

1. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.0 out of 10, Very good, (5 reviews)
The price is ￥70,178
￥84,234 total
includes taxes & fees
Sep 21 - Sep 22
Clifford Luxury Retreat 3BR Self Check In Home
Interior

2. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (252 reviews)
"Wonderful!!"
United States
Huynh
The price is ￥15,088
￥16,853 total
includes taxes & fees
Sep 23 - Sep 24
Residences at Solomon Pond
Dining

3. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is ￥33,451
￥40,208 total
includes taxes & fees
Oct 12 - Oct 13
Zen Inspired Retreat with Private Forest Trails
Exterior

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 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. "
United States
Mateo A.
The price is ￥19,650
￥29,303 total
includes taxes & fees
Sep 21 - Sep 22
Wizard's Roost at Underhill Hollow
Interior

5. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is ￥19,650
￥30,200 total
includes taxes & fees
Sep 22 - Sep 23
The Tree House at Underhill Hollow
Property grounds

6. 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 ￥77,975
￥95,111 total
includes taxes & fees
Oct 14 - Oct 15
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Property grounds

7. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥19,650
￥29,303 total
includes taxes & fees
Oct 2 - Oct 3
SteamPunk Bunk House and Intergalactic Way Station
Terrace/patio

8. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (28 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
The price is ￥70,178
￥115,598 total
includes taxes & fees
Sep 26 - Sep 27
Stunning Lakefront Escape! Book Your Dream Getaway!
2 bedrooms, WiFi (free)

9. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is ￥23,720
￥44,960 total
includes taxes & fees
Sep 21 - Sep 22
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Dining

10. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.8 out of 10, Exceptional, (6 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is ￥25,101
￥58,038 total
includes taxes & fees
Sep 20 - Sep 21
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (90 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is ￥74,076
￥120,549 total
includes taxes & fees
Sep 20 - Sep 21
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Coffee/tea maker, fridge, microwave, oven

12. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (20 reviews)
"Perfect location"
United States
Harmony F.
The price is ￥42,886
￥80,141 total
includes taxes & fees
Sep 22 - Sep 23
Spacious 4-bedroom with four and half bathrooms
Exterior detail

13. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is ￥38,208
￥48,930 total
includes taxes & fees
Sep 23 - Sep 24
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

14. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is ￥27,369
￥40,138 total
includes taxes & fees
Sep 21 - Sep 22
Dove Cabin up in the Trees
Property grounds

15. 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 ￥109,816
￥133,880 total
includes taxes & fees
Oct 14 - Oct 15
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Exterior

16. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is ￥18,387
￥33,544 total
includes taxes & fees
Sep 22 - Sep 23
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Living area

17. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is ￥10,731
￥15,872 total
includes taxes & fees
Oct 16 - Oct 17
Clean & Cozy Private- 3 floor_R 4
Dining

18. Lovely Historic Vintage home. Remodeled inside.

Lovely Historic Vintage home. Remodeled inside.
Johnston
9.4 out of 10, Exceptional, (50 reviews)
"My host was awesome. The house was is a nice neighborhood everything we needs so close. "
United States
Tina N.
The price is ￥27,790
￥69,104 total
includes taxes & fees
Sep 21 - Sep 22
Lovely Historic Vintage home. Remodeled inside.
Interior

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is ￥33,545
￥43,569 total
includes taxes & fees
Sep 22 - Sep 23
Game Room + Bar Lounge, 35 Min to Boston
Smart TV

20. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is ￥25,124
￥46,355 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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

DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

10/10 Excellent
"Great hotel. Clean. Large room. Well located."
Dominic 4-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Boston - Westborough

Find out more about Douglas

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Look no further and take a look at our great range of rental properties in Douglas!

Frequently asked questions

Are there vacation rentals in Douglas?

Yes, we give you a choice of vacation rentals in Douglas near Breezy Picnic Grounds & Waterslides, or you can choose a secluded option if you'd like a relaxing place to stay. Douglas is known for its parks.

What's the top vacation rental in Douglas?

Chalet on the Hill 5 minutes from downtown: This vacation home rental outside of Douglas offers a fireplace, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Douglas?

Family-friendly attractions include Breezy Picnic Grounds & Waterslides, whereas Manchaug Pond is a spot to enjoy the outdoors. Buck Hill Management Area and Blissful Meadows Golf Club are a couple of places you'll find in the larger area.

What’s a vacation rental in Douglas like?

Vacation rentals are private properties where you can stay for a long or short time in Douglas. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips or small group gatherings.