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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Dudley vacation rentals

Interior

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 ￥19,436
￥29,871 total
includes taxes & fees
Sep 22 - Sep 23
The Tree House at Underhill Hollow
Exterior

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (25 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 ￥19,436
￥28,984 total
includes taxes & fees
Sep 17 - Sep 18
Wizard's Roost at Underhill Hollow
Property grounds

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 ￥19,436
￥28,984 total
includes taxes & fees
Sep 27 - Sep 28
SteamPunk Bunk House and Intergalactic Way Station
Interior

4. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
7.0 out of 10, Good, (2 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is ￥14,654
￥19,815 total
includes taxes & fees
Sep 17 - Sep 18
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Interior

5. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is ￥23,270
￥48,865 total
includes taxes & fees
Sep 24 - Sep 25
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Property grounds

6. 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 ￥77,565
￥94,611 total
includes taxes & fees
Oct 14 - Oct 15
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Exterior

7. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is ￥27,071
￥39,863 total
includes taxes & fees
Sep 17 - Sep 18
Dove Cabin up in the Trees
Exterior

8. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (6 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is ￥18,186
￥33,178 total
includes taxes & fees
Sep 22 - Sep 23
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Living area

9. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
The price is ￥26,377
￥37,500 total
includes taxes & fees
Sep 17 - Sep 18
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Living area

10. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is ￥10,611
￥15,695 total
includes taxes & fees
Oct 16 - Oct 17
Clean & Cozy Private- 3 floor_R 4
Property grounds

11. 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)
"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 ￥23,600
￥29,980 total
includes taxes & fees
Sep 17 - Sep 18
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

12. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (39 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is ￥18,016
￥42,776 total
includes taxes & fees
Sep 17 - Sep 18
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Interior

13. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is ￥6,941
￥19,642 total
includes taxes & fees
Sep 18 - Sep 19
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior detail

14. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is ￥37,791
￥48,396 total
includes taxes & fees
Sep 19 - Sep 20
Cozy 1-bedroom cottage in serene Pomfret.
Property grounds

15. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (18 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is ￥10,412
￥32,798 total
includes taxes & fees
Sep 24 - Sep 25
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Terrace/patio

16. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is ￥20,053
￥50,325 total
includes taxes & fees
Sep 24 - Sep 25
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Dining

17. 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 ￥73,269
￥119,544 total
includes taxes & fees
Sep 17 - Sep 18
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (23 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is ￥39,558
￥121,409 total
includes taxes & fees
Sep 17 - Sep 18
Lake House in Sturbridge w/All the Views!
Exterior

19. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
The price is ￥16,906
￥40,266 total
includes taxes & fees
Sep 17 - Sep 18
Treehouse - Countryside - Farm Animals - Fire Pit
Property grounds

20. 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.
The price is ￥107,975
￥131,635 total
includes taxes & fees
Oct 14 - Oct 15
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
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

Spark By Hilton Northborough

Spark By Hilton Northborough

10/10 Excellent
"Nice clean place"
Debra 1-night trip
Posted 14 hours ago
Spark By Hilton Northborough

Find out more about Dudley

Search for holiday rentals in Dudley on Expedia! You can easily find your home rentals, villas, holiday apartments in Dudley using one of the methods below:

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Look no further and take a look at our great range of rental properties in Dudley!

Frequently asked questions

Are there vacation rentals in Dudley?

Yes, there are vacation rentals near popular attractions in Dudley, or you can choose a more remote option if you're looking for a relaxing stay. Dudley is known for its restaurants.

What's the top vacation rental that Dudley has to offer?

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: Visitors like this Dudley vacation home rental. It is located in a rural location and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Dudley?

Choose from 3 Expedia vacation rentals in Dudley for a memorable vacation.

What’s there to see and do in Dudley?

Stevens Park and Berthol Field are a couple of lovely local spots to get outside and enjoy nature. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

What’s a vacation rental in Dudley like?

Vacation rentals are private properties you can book for a long or short time in Dudley. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.