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Check prices for these dates

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

Our top choices for Dudley vacation 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 ￥22,386
￥32,780 total
includes taxes & fees
Jun 21 - Jun 22
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 ￥26,623
￥42,130 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥30,221
￥37,383 total
includes taxes & fees
Jun 7 - Jun 8
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.
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 ￥20,147
￥30,964 total
includes taxes & fees
Jun 18 - Jun 19
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 ￥20,147
￥30,045 total
includes taxes & fees
Jun 18 - Jun 19
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.
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 ￥25,584
￥41,542 total
includes taxes & fees
Jun 6 - Jun 7
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 ￥31,980
￥66,430 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥43,973
￥81,621 total
includes taxes & fees
Jun 10 - Jun 11
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 ￥29,422
￥37,152 total
includes taxes & fees
Jun 8 - Jun 9
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 ￥29,582
￥110,634 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥23,921
￥50,695 total
includes taxes & fees
Jun 8 - Jun 9
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 ￥26,348
￥29,898 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥47,970
￥60,370 total
includes taxes & fees
Jun 9 - Jun 10
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 ￥71,955
￥118,046 total
includes taxes & fees
Jun 7 - Jun 8
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 ￥63,960
￥76,902 total
includes taxes & fees
Jun 17 - Jun 18
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 ￥50,848
￥79,774 total
includes taxes & fees
Jun 8 - Jun 9
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 ￥39,975
￥52,340 total
includes taxes & fees
Jun 6 - Jun 7
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 ￥75,953
￥121,844 total
includes taxes & fees
Jun 9 - Jun 10
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.
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Top Dudley Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"Beautiful Inn. A wonderful surprise. Spacious room and fine restaurants."
Larry 1-night trip
Posted less than an hour ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Dudley

Dudley Vacation Homes information

Number of reviews
307
Accommodation
104 Vacation Homes
Lowest Price
￥29,898
Highest Price
￥121,844