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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Dudley holiday homes

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 £146
includes taxes & fees
13 Sept - 14 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, (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 £142
includes taxes & fees
11 Sept - 12 Sept
Wizard's Roost at Underhill Hollow
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.

3. 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 £142
includes taxes & fees
13 Sept - 14 Sept
SteamPunk Bunk House and Intergalactic Way Station
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

4. 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)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is £156
includes taxes & fees
13 Sept - 14 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (89 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is £565
includes taxes & fees
11 Sept - 12 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A deck with outdoor furniture overlooking a lake, surrounded by trees.

6. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 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 £546
includes taxes & fees
13 Sept - 14 Sept
Stunning Lakefront Escape! Book Your Dream Getaway!

7. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (4 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is £194
includes taxes & fees
20 Sept - 21 Sept
Cottage by the Castle – Downtown Spencer
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

8. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (18 reviews)
"Perfect location"
United States
Harmony F.
The price is £371
includes taxes & fees
14 Sept - 15 Sept
Spacious 4-bedroom with four and half bathrooms
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

9. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is £193
includes taxes & fees
11 Sept - 12 Sept
Angel Sky Challenge
A window with a view of a grassy field and trees.

10. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is £228
includes taxes & fees
13 Sept - 14 Sept
Spacious, unique barn with beautiful views.
A bedroom with a large mirror, a bed with floral bedding, a standing lamp, and a window with curtains.

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.4 out of 10, Exceptional, (36 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is £211
includes taxes & fees
21 Sept - 22 Sept
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (24 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 £250
includes taxes & fees
24 Sept - 25 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A bar area with a counter, two green chairs, a refrigerator, and a neon sign.

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is £211
includes taxes & fees
17 Sept - 18 Sept
Game Room + Bar Lounge, 35 Min to Boston
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

14. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is £418
includes taxes & fees
13 Sept - 14 Sept
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

15. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is £440
includes taxes & fees
13 Sept - 14 Sept
6 Beds Home w/Game Room Perfect for Groups
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

16. 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 £392
includes taxes & fees
13 Sept - 14 Sept
Clifford Luxury Retreat 3BR Self Check In Home
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

17. 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 £1,185
includes taxes & fees
13 Sept - 14 Sept
Sleeps 15 • Pool • Retreat
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

18. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (1 review)
"The house was located in a quiet, nice, pleasant, neighborhood. The rooms were spacious and comfortable. The house was very clean and the beds were comfortable. The house was located near all kinds of stores, pharmacy’s, and good restaurants. I’d I had to make a negative comment it would be that all the bedrooms were on the second floor which was tough for two of our party. The property owner was quick to respond to questions we had. Overall, a very pleasant stay."
United States
Samantha R.
The price is £408
includes taxes & fees
13 Sept - 14 Sept
4-bedroom house in nice Holden with WiFi, AC
A residential property with a grassy yard, a tree, and a house in the background.

19. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is £635
includes taxes & fees
6 Oct - 7 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
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
"Great hotel! Very clean rooms and the AC worked great, was cool all night. Rooms are very spacious, nice bathrooms with good shower pressure and hot water. Loved the pool and hot tub, that was the highlight of our trip! We will be back."
Rachel 2-night trip
Posted 1 hour ago
Wellsworth Hotel

Find out more about Dudley

Dudley Holiday Homes information

Number of reviews
321
Accommodation
107 Holiday Homes
Lowest Price
£142
Highest Price
£1,185