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Dudley Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Dudley holiday rentals

Iron/ironing board, WiFi, bed sheets

1. 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
The price is HK$1,341
HK$1,907 total
includes taxes & fees
28 Aug - 29 Aug
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Interior

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is HK$1,603
HK$2,095 total
includes taxes & fees
13 Sept - 14 Sept
Game Room + Bar Lounge, 35 Min to Boston
Interior

3. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$988
HK$1,535 total
includes taxes & fees
19 Aug - 20 Aug
The Tree House at Underhill Hollow
Exterior

4. 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 HK$989
HK$1,482 total
includes taxes & fees
25 Aug - 26 Aug
Wizard's Roost at Underhill Hollow
Property grounds

5. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$989
HK$1,482 total
includes taxes & fees
19 Aug - 20 Aug
SteamPunk Bunk House and Intergalactic Way Station
Terrace/patio

6. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is HK$3,531
HK$5,832 total
includes taxes & fees
30 Aug - 31 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

7. 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 HK$3,922
HK$6,336 total
includes taxes & fees
17 Sept - 18 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior

8. 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, (6 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$1,137
HK$1,979 total
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior detail

9. 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 HK$1,922
HK$2,485 total
includes taxes & fees
17 Sept - 18 Sept
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

10. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (34 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is HK$1,377
HK$2,044 total
includes taxes & fees
24 Aug - 25 Aug
Dove Cabin up in the Trees
TV, fireplace

11. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is HK$6,883
HK$12,788 total
includes taxes & fees
9 Sept - 10 Sept
Sleeps 15 • Pool • Retreat
Interior

12. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is HK$2,825
HK$7,258 total
includes taxes & fees
3 Sept - 4 Sept
Lake House in Sturbridge w/All the Views!
Interior

13. 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$1,593
HK$3,042 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Coffee/tea maker, fridge, microwave, oven

14. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location"
United States
Harmony F.
The price is HK$2,157
HK$4,058 total
includes taxes & fees
9 Sept - 10 Sept
Spacious 4-bedroom with four and half bathrooms
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 HK$1,796
HK$2,069 total
includes taxes & fees
19 Aug - 20 Aug
Cottage by the Castle – Downtown Spencer
Interior

16. 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 HK$463
HK$692 total
includes taxes & fees
19 Aug - 20 Aug
Modern 1-bedroom apartment in peaceful Sturbridge with AC
3 bedrooms, desk, iron/ironing board, free WiFi

17. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
9.0 out of 10, Wonderful, (2 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is HK$3,530
HK$4,262 total
includes taxes & fees
24 Aug - 25 Aug
Clifford Luxury Retreat 3BR Self Check In Home
Property grounds

18. 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
9.4 out of 10, Exceptional, (8 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is HK$1,167
HK$1,497 total
includes taxes & fees
19 Aug - 20 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Dining

19. 12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.6 out of 10, Exceptional, (4 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is HK$1,624
HK$3,384 total
includes taxes & fees
19 Aug - 20 Aug
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (23 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$1,814
HK$3,365 total
includes taxes & fees
24 Aug - 25 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
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
"First choice to stay when I’m in the area"
Matthew 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:

  • View our selection of featured holiday rentals in Dudley
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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 in Dudley close to TriState Speedway, 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?

Home Away from Home!: This holiday home rental outside of Dudley 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

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 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 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.