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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (41 reviews)
"Great space, lots of fun."
United States
Douglas C.
$172 nightly
The price is $195
Sep 3 - Sep 4
Total with taxes and fees
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, (24 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.
$166 nightly
The price is $188
Sep 3 - Sep 4
Total with taxes and fees
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.
$166 nightly
The price is $188
Sep 3 - Sep 4
Total with taxes and fees
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.
$75 nightly
The price is $84
Sep 4 - Sep 5
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Exterior

5. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (35 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
$247 nightly
The price is $261
Sep 2 - Sep 3
Total with taxes and fees
Dove Cabin up in the Trees
Exterior

6. 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.
$223 nightly
The price is $252
Sep 2 - Sep 3
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Interior

7. 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.
$347 nightly
The price is $388
Sep 13 - Sep 14
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Iron/ironing board, WiFi, bed sheets

8. 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
$229 nightly
The price is $242
Sep 4 - Sep 5
Total with taxes and fees
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Property grounds

9. 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
$188 nightly
The price is $213
Sep 10 - Sep 11
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Property grounds

10. 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)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
$176 nightly
The price is $196
Sep 2 - Sep 3
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior detail

11. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
$279 nightly
The price is $316
Sep 13 - Sep 14
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Living area

12. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
$100 nightly
The price is $115
Sep 16 - Sep 17
Total with taxes and fees
Clean & Cozy Private- 3 floor_R 4
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$124 nightly
The price is $139
Sep 2 - Sep 3
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Terrace/patio

14. 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, (48 reviews)
"Great place, amazing lake!"
United States
megan g.
$292 nightly
The price is $330
Sep 11 - Sep 12
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

15. 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.
$332 nightly
The price is $376
Sep 17 - Sep 18
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Exterior

16. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (4 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
$236 nightly
The price is $238
Sep 3 - Sep 4
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
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.
$685 nightly
The price is $775
Sep 6 - Sep 7
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Terrace/patio

18. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
$656 nightly
The price is $742
Sep 6 - Sep 7
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (23 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
$260 nightly
The price is $294
Sep 3 - Sep 4
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior

20. 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.
$267 nightly
The price is $302
Sep 2 - Sep 3
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
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
"Great bake shop and coffee in the morning. Only complaint is that they need to paint lines for parking near the hotel rooms. People park wherever they want and take up 2 spaces. It's distressing to come back late and have no place to park."
Barbara 3-night trip
Posted 14 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Dudley

Everything you need to know about Dudley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dudley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dudley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dudley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dudley. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Dudley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $84 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Dudley rentals

At Expedia, we put the best Dudley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Dudley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dudley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dudley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Home Away from Home!: Visitors like this Dudley vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

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.