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Douglas Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Douglas vacation rentals

A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

1. 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.
$243 nightly
The price is $258
Oct 19 - Oct 20
Total with taxes and fees
Zen Inspired Retreat with Private Forest Trails
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

2. 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)
$508 nightly
The price is $537
Oct 12 - Oct 13
Total with taxes and fees
Clifford Luxury Retreat 3BR Self Check In Home
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

3. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
$171 nightly
The price is $194
Oct 13 - Oct 14
Total with taxes and fees
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

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.
$166 nightly
The price is $188
Oct 12 - Oct 13
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A bedroom with a wooden bed, large windows, and a view of greenery outside.

5. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
$339 nightly
The price is $384
Oct 12 - Oct 13
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
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.

6. 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.
$166 nightly
The price is $188
Oct 12 - Oct 13
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A modern hotel lobby with a seating area, a bar, and a kitchen.

7. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (254 reviews)
"Wonderful!!"
United States
Huynh
$106 nightly
The price is $118
Oct 21 - Oct 22
Total with taxes and fees
Residences at Solomon Pond
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

8. 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.
$564 nightly
The price is $630
Oct 14 - Oct 15
Total with taxes and fees
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A kitchen with wooden cabinets, a window with a view, a vase with flowers, and framed pictures on the windowsill.

9. 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, (7 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
$378 nightly
The price is $400
Oct 11 - Oct 12
Total with taxes and fees
12B-Cozy 3BR Apartment with Koi Pond in Worcester
A two-story house with a front porch, stone steps, and a driveway.

10. 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)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$194 nightly
The price is $220
Oct 19 - Oct 20
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

11. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
$190 nightly
The price is $212
Oct 20 - Oct 21
Total with taxes and fees
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

12. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"10/10 great place to stay"
United States
Tyler B.
$449 nightly
The price is $514
Oct 14 - Oct 15
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Living area

13. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
$349 nightly
The price is $399
Oct 12 - Oct 13
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

14. Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
Franklin Plantation
9.4 out of 10, Exceptional, (3 reviews)
"The communication was wonderful. There were some things that needed to be addressed and they were.We would definitely rent again! The space is very spacious and clean"
United States
Anonymous traveler
$272 nightly
The price is $311
Nov 9 - Nov 10
Total with taxes and fees
Newly Refreshed 3bd Spacious Unit Minutes from 290
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

15. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
$187 nightly
The price is $214
Oct 13 - Oct 14
Total with taxes and fees
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A modern kitchen with stainless steel appliances, wooden ceiling, and a dining area with a wooden table and chairs.

16. Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Lincoln
10.0 out of 10, Exceptional, (32 reviews)
"Everything was clean and welcoming. Kitchen had everything you need to cook, make coffee, etc. charming and comfortable "
United States
Lindsey D.
$192 nightly
The price is $219
Oct 12 - Oct 13
Total with taxes and fees
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
A living room with two sofas, a coffee table, and a bookshelf.

17. Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
$210 nightly
The price is $240
Oct 20 - Oct 21
Total with taxes and fees
Heart of Shrewsbury St – 2BR Stay
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

18. 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
$433 nightly
The price is $496
Oct 18 - Oct 19
Total with taxes and fees
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

19. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
$100 nightly
The price is $115
Oct 12 - Oct 13
Total with taxes and fees
Clean & Cozy Private-3 floor_R 2
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

20. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$164 nightly
The price is $183
Oct 11 - Oct 12
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Always a great stay. Convenient and comfortable."
Sophie 1-night trip
Posted 1 hour ago
Wellsworth Hotel

Find out more about Douglas

Everything you need to know about Douglas vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Douglas vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Douglas vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Douglas vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Douglas. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Douglas in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Douglas rentals

At Expedia, we put the best Douglas vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Douglas rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Douglas vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Douglas. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Lovely Historic Vintage home. Remodeled inside.: This vacation home rental outside of Douglas is located on a river and has a fireplace, a garden, and a barbecue grill to put you at ease 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 Buck Hill Management Area is a spot to enjoy the outdoors. Manchaug Pond 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.