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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Dudley vacation rentals

Interior

1. 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 ￥19,832
￥30,480 total
includes taxes & fees
Aug 3 - Aug 4
The Tree House at Underhill Hollow
Exterior

2. 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 ￥19,832
￥29,575 total
includes taxes & fees
Aug 13 - Aug 14
Wizard's Roost 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, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥19,832
￥29,575 total
includes taxes & fees
Aug 3 - Aug 4
SteamPunk Bunk House and Intergalactic Way Station
Interior

4. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is ￥9,417
￥14,084 total
includes taxes & fees
Aug 3 - Aug 4
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Living area

5. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is ￥10,766
￥15,924 total
includes taxes & fees
Aug 3 - Aug 4
Clean & Cozy Private- 3 floor_R 4
Exterior

6. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (32 reviews)
"Sue is a great host, making necessary adjustments to suit the circumstances, generous and flexible. The dove cabin is so sweet, comfortable beds, cozy stove and fully equipped kitchen. And lovely porch! There’s a really cool swing on the way down to a peaceful pond!"
United States
kathryn m.
The price is ￥27,624
￥40,512 total
includes taxes & fees
Aug 5 - Aug 6
Dove Cabin up in the Trees
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (5 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 ￥24,507
￥41,484 total
includes taxes & fees
Aug 31 - Sep 1
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior

8. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is ￥17,314
￥32,267 total
includes taxes & fees
Aug 26 - Aug 27
The Carriage House at Chaprae Hall
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is ￥9,444
￥22,680 total
includes taxes & fees
Aug 7 - Aug 8
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Terrace/patio

10. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

11. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is ￥13,535
￥37,113 total
includes taxes & fees
Aug 3 - Aug 4
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Exterior detail

12. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is ￥38,563
￥49,384 total
includes taxes & fees
Aug 5 - Aug 6
Cozy 1-bedroom cottage in serene Pomfret.
Smart TV

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.
The price is ￥28,497
￥67,743 total
includes taxes & fees
Aug 3 - Aug 4
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Interior

14. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
10.0 out of 10, Exceptional, (1 review)
The price is ￥23,681
￥57,369 total
includes taxes & fees
Aug 4 - Aug 5
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Exterior

15. 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 ￥36,021
￥41,012 total
includes taxes & fees
Aug 6 - Aug 7
Cottage by the Castle – Downtown Spencer
Property grounds

16. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is ￥26,719
￥33,410 total
includes taxes & fees
Aug 4 - Aug 5
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Smart TV

17. Serenity meets Taradise

Serenity meets Taradise
Union
The price is ￥16,999
￥27,222 total
includes taxes & fees
Aug 14 - Aug 15
Serenity meets Taradise
Dining

18. 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 ￥23,942
￥55,717 total
includes taxes & fees
Aug 17 - Aug 18
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Terrace/patio

19. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is ￥70,830
￥116,673 total
includes taxes & fees
Aug 13 - Aug 14
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

20. 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 ￥75,815
￥123,379 total
includes taxes & fees
Aug 2 - Aug 3
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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 Dudley Hotel Reviews

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Beautiful building, clean room. Staff were so friendly and helpful, and the pool was awesome!"
Kristy 1-night trip
Posted 3 hours ago
Wellsworth Hotel

Find out more about Dudley

Search for holiday rentals in Dudley on Expedia! You can easily find your home rentals, villas, holiday apartments in Dudley using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Dudley?

Yes, there are vacation rentals in Dudley near TriState Speedway, or you can go with a secluded option if you want a relaxing stay. Dudley is known for its restaurants.

What's the top vacation rental that Dudley has to offer?

Home Away from Home!: Visitors like this Dudley vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

How many vacation rentals are there in Dudley?

Choose from 3 Expedia vacation rentals in Dudley for a memorable vacation.

What’s there to see and do in Dudley?

Stevens Park and Berthol Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include TriState Speedway. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

What’s a vacation rental in Dudley like?

Vacation rentals are private properties you can book for a long or short time in Dudley. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies 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 an attractive choice for family gatherings.