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Check prices for these dates

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

Our top choices for Dudley vacation 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, (43 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AED 463
AED 711 total
includes taxes & fees
7 Oct - 8 Oct
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 AED 463
AED 690 total
includes taxes & fees
13 Oct - 14 Oct
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 AED 463
AED 690 total
includes taxes & fees
7 Oct - 8 Oct
SteamPunk Bunk House and Intergalactic Way Station
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

4. 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 AED 1,837
AED 2,314 total
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

5. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
The price is AED 918
AED 2,855 total
includes taxes & fees
7 Oct - 8 Oct
Lake House in Sturbridge w/All the Views!
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

7. 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, (10 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 AED 643
AED 812 total
includes taxes & fees
26 Oct - 27 Oct
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.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,377
AED 2,373 total
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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 AED 588
AED 950 total
includes taxes & fees
12 Oct - 13 Oct
Angel Sky Challenge
The Cottage is nestled next to the historic Sagendorph Mansion.

10. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is AED 841
AED 965 total
includes taxes & fees
12 Oct - 13 Oct
Cottage by the Castle – Downtown Spencer
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is AED 614
AED 787 total
includes taxes & fees
7 Oct - 8 Oct
Game Room + Bar Lounge, 35 Min 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.
The price is AED 1,010
AED 1,875 total
includes taxes & fees
18 Oct - 19 Oct
Spacious 4-bedroom with four and half bathrooms
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

13. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 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 AED 3,636
AED 6,503 total
includes taxes & fees
8 Oct - 9 Oct
Sleeps 15 • Pool • Retreat
A window with a view of a grassy field and trees.

14. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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 AED 727
AED 1,119 total
includes taxes & fees
12 Oct - 13 Oct
Spacious, unique barn with beautiful views.
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

15. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A modern interior with a kitchen, dining area, and living space.

16. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
10.0 out of 10, Exceptional, (1 review)
"Edgar was very responsive and easy to work with. The unit was very clean and well kept. I would definitely stay there again."
United States
debra l.
The price is AED 667
AED 2,125 total
includes taxes & fees
7 Oct - 8 Oct
6 Beds Home w/Game Room Perfect for Groups
A living room with a sofa, a clock, a floor lamp, and a rug.

17. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (55 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is AED 592
AED 1,100 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

19. 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)
The price is AED 1,653
AED 1,972 total
includes taxes & fees
7 Oct - 8 Oct
Clifford Luxury Retreat 3BR Self Check In Home
A two-story residential building with a front porch, a satellite dish, and a small front yard.

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

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
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

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

8/10 Good
"Na"
Cassandra 1-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Sturbridge by IHG