Default HTG hotel image

Dudley Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Dudley holiday rentals

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. 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 HK$988
HK$1,519 total
includes taxes & fees
27 Sept - 28 Sept
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. 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 HK$988
HK$1,474 total
includes taxes & fees
27 Sept - 28 Sept
Wizard's Roost at Underhill Hollow
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$353
HK$999 total
includes taxes & fees
26 Sept - 27 Sept
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
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.

4. 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 HK$988
HK$1,427 total
includes taxes & fees
29 Sept - 30 Sept
SteamPunk Bunk House and Intergalactic Way Station
A two-story house with a front porch, stone steps, and a driveway.

5. 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 HK$946
HK$1,695 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A wooden cabin with a glass upper floor, surrounded by a forest.

6. 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 HK$1,376
HK$2,035 total
includes taxes & fees
27 Sept - 28 Sept
Dove Cabin up in the Trees
A bedroom with a wooden bed, large windows, and a view of greenery outside.

7. 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.
The price is HK$1,961
HK$2,917 total
includes taxes & fees
27 Sept - 28 Sept
Rustic Farmette Studio with Hot Tub & Pool
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 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 HK$602
HK$1,775 total
includes taxes & fees
27 Sept - 28 Sept
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
7.0 out of 10, Good, (2 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is HK$745
HK$911 total
includes taxes & fees
27 Sept - 28 Sept
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is HK$957
HK$2,479 total
includes taxes & fees
29 Sept - 30 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

11. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,176
HK$2,470 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

12. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
The price is HK$628
HK$899 total
includes taxes & fees
27 Sept - 28 Sept
Clean & Cozy Private-3 floor_R 2
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

13. 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 HK$3,921
HK$4,941 total
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a painting on the wall, and a carpet with a geometric pattern.

14. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
The price is HK$1,341
HK$1,898 total
includes taxes & fees
27 Sept - 28 Sept
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

15. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is HK$1,267
HK$2,634 total
includes taxes & fees
28 Sept - 29 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A house with a white porch, a black door, and a window with a white frame.

16. 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 HK$1,921
HK$2,461 total
includes taxes & fees
27 Sept - 28 Sept
Cozy 1-bedroom cottage in serene Pomfret.
A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

17. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is HK$1,512
HK$2,884 total
includes taxes & fees
27 Sept - 28 Sept
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

18. 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 HK$1,167
HK$3,023 total
includes taxes & fees
27 Sept - 28 Sept
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

19. 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, (9 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is HK$1,242
HK$1,519 total
includes taxes & fees
28 Sept - 29 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

20. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is HK$816
HK$2,038 total
includes taxes & fees
30 Sept - 1 Oct
Large 3BD 1st Floor Apartment Minutes from 290
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dudley Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"My husband and I had a wonderful stay in the Chamberlin House. The staff was extremely helpful and kind. Our room was clean and very tastefully decorated, in an "updated" classic colonial style. The grounds were absolutely gorgeous and we thoroughly enjoyed a delicious dinner in the Publick House restaurant. The breakfast pastries in the onsite bakery were outstanding. We would never hesitate to stay at Publick House again."
Nancy 1-night trip
Posted 6 hours ago
Publick House Historic Inn and Country Motor Lodge

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:

  • View our selection of featured holiday rentals in Dudley
  • Use the map to find apartments and other holiday homes in the Dudley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Dudley while they last

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

Frequently asked questions

Are there holiday rentals in Dudley?

Yes, there are holiday rentals close to the most popular sights in Dudley, or you can select a more secluded option if you're looking for a relaxing stay. Dudley is known for its restaurants.

What are some of the best holiday rentals that Dudley has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This holiday home rental outside of Dudley is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Dudley?

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

What’s there to see and do in Dudley?

Stevens Park and Berthol Field are a couple of lovely local spots to get outside and enjoy nature. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

What’s a holiday rental in Dudley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dudley. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family getaway.