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Holiday Homes in Dudley

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AU$279
includes taxes & fees
26 Oct - 27 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)
"Great stay!!"
United States
Elizabeth G.
The price is AU$271
includes taxes & fees
25 Oct - 26 Oct
Wizard's Roost at Underhill Hollow
A room with two wicker chairs and a small round table, a large window, and a red door.

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$271
includes taxes & fees
1 Nov - 2 Nov
SteamPunk Bunk House and Intergalactic Way Station
A hotel with a central building, outdoor seating area, and a covered patio.

4. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveller
The price is AU$699
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
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, (94 reviews)
"Beautiful lake house. The dock with the kayaks and paddle boat made it so much fun for the kids. The dock isnt far from the house but there a decent hill down to it. Totally manageable for most people though. The open house concept kitchen area made it great for everyone to be together."
United States
Amanda S.
The price is AU$892
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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, (25 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 AU$1,229
includes taxes & fees
25 Oct - 26 Oct
Lake House in Sturbridge w/All the Views!
A round metal fire pit with grilling tools and a red chair in the background.

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, (12 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 AU$305
includes taxes & fees
27 Oct - 28 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A two-story house with a central entrance, a brick foundation, and a large front yard.

8. 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 AU$365
includes taxes & fees
24 Oct - 25 Oct
Angel Sky Challenge
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

9. 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.
The price is AU$586
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
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, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AU$367
includes taxes & fees
25 Oct - 26 Oct
Cottage by the Castle – Downtown Spencer
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

11. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (40 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 AU$2,374
includes taxes & fees
26 Oct - 27 Oct
Sleeps 15 • Pool • Retreat
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)
"Great, clean location to stay."
United States
Mike O.
The price is AU$712
includes taxes & fees
25 Oct - 26 Oct
Spacious 4-bedroom with four and half bathrooms
A living room with a black leather sofa, white curtains, a clock on the wall, and a window with a view of trees.

13. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is AU$377
includes taxes & fees
25 Oct - 26 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A modern interior with a kitchen, dining area, and living space.

14. 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, (2 reviews)
"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.
6 Beds Home w/Game Room Perfect for Groups
A hotel room with a bed, bedside table, lamp, potted plant, and a desk with a chair.

15. 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
The price is AU$699
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A window with a view of a grassy field and trees.

16. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (8 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 AU$431
includes taxes & fees
28 Oct - 29 Oct
Spacious, unique barn with beautiful views.
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

17. 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, (3 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is AU$726
includes taxes & fees
26 Oct - 27 Oct
4-bedroom house in nice Holden with WiFi, AC
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

18. 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 AU$752
includes taxes & fees
25 Oct - 26 Oct
Clifford Luxury Retreat 3BR Self Check In Home
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

8/10 Good
"Room was great for the price and the complimentary pastries and coffee for breakfast were great. Only dissappointment were the drinks and food quality at dinner...a bit sub par. On the otherhand, the restaurant was very cozy. Next time we stay, we'll probably go elsewhere for dinner."
David 1-night trip
Posted 2 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Dudley

Dudley Holiday Homes information

Number of reviews
412
Accommodation
107 Holiday Homes
Lowest Price
AU$271
Highest Price
AU$2,374