Holiday Homes in Dudley

  • 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
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Dudley holiday homes

Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is NZ$317
includes taxes & fees
3 June - 4 June
Wizard's Roost at Underhill Hollow
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 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 NZ$444
includes taxes & fees
6 June - 7 June
Spacious, unique barn with beautiful views.
Sailing, kayaking, fishing

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Stafford Springs
The price is NZ$394
includes taxes & fees
3 June - 4 June
Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Smart TV

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.6 out of 10, Exceptional, (47 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is NZ$486
includes taxes & fees
3 June - 4 June
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is NZ$326
includes taxes & fees
3 June - 4 June
The Tree House at Underhill Hollow
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is NZ$317
includes taxes & fees
3 June - 4 June
SteamPunk Bunk House and Intergalactic Way Station
Bathroom

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

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (32 reviews)
"Lovely and great location "
United States
Kimberlee K.
The price is NZ$486
includes taxes & fees
8 June - 9 June
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Interior

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 NZ$438
includes taxes & fees
3 June - 4 June
Angel Sky Challenge
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (1 review)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is NZ$696
includes taxes & fees
7 June - 8 June
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
The price is NZ$860
includes taxes & fees
3 June - 4 June
Spacious 4-bedroom with four and half bathrooms
Property grounds

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
8.8 out of 10, Excellent, (3 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is NZ$390
includes taxes & fees
8 June - 9 June
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is NZ$1,147
includes taxes & fees
7 June - 8 June
6 Beds Home w/Game Room Perfect for Groups
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (21 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is NZ$557
includes taxes & fees
10 June - 11 June
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
The price is NZ$315
includes taxes & fees
7 June - 8 June
Cottage by the Castle – Downtown Spencer
Property grounds

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 NZ$632
includes taxes & fees
26 June - 27 June
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is NZ$1,239
includes taxes & fees
3 June - 4 June
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is NZ$802
includes taxes & fees
3 June - 4 June
Clifford Luxury Retreat 3BR Self Check In Home
Private kitchen

4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
The price is NZ$794
includes taxes & fees
3 June - 4 June
4-bedroom house in nice Holden with WiFi, AC
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
The price is NZ$494
includes taxes & fees
3 June - 4 June
Cozy 3-bedroom house in serene Worcester with fitness room and office
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (84 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is NZ$1,272
includes taxes & fees
3 June - 4 June
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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

La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

6/10 Okay
"I want to praise the staff they are very attentive, I stayed on the second floor and I could not handle the smell of the Dogs, I ask to switch my room but it was very stink of dog smell, I try to get a good night rest, as I came to support my brother who just found out that he had cancer, and I was tired every day I visited him, the car was so load on the road which keep me awake and the truck that was being use to fix the building. My sister get the 3rd floor and it was not stink but the second floor out very bad. When I leave the hotel to go outside I have to spray my whole clothes with purfume so I don’t smell of a dog that I don’t have."
Marian 4-night trip
Posted 2 hours ago
La Quinta Inn by Wyndham Auburn Worcester

Find out more about Dudley

Dudley Holiday Homes information

Number of reviews
307
Accommodation
101 Holiday Homes
Lowest Price
NZ$315
Highest Price
NZ$1,272