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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Dudley vacation rentals

Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Jul 16 - Jul 17
Total with taxes and fees
Dove Cabin up in the Trees
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, (48 reviews)
"Convenient location for our stay. Great communication by host. Bedrooms were spacious and clean. Large driveway for plenty of parking. Convenient to many shopping options and beautiful park close by. "
United States
Theresa 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, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
$171 nightly
The price is $194
Jul 19 - Jul 20
Total with taxes and fees
The Tree House at Underhill Hollow
Private kitchen

Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
$100 nightly
The price is $115
Jul 14 - Jul 15
Total with taxes and fees
Clean & Cozy Private room - 3 floor_R 1
Terrace/patio

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, (45 reviews)
"Very nice area."
United States
maureen p.
$313 nightly
The price is $354
Jul 15 - Jul 16
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Jul 14 - Jul 15
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (23 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
Jul 19 - Jul 20
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Exterior

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (34 reviews)
"The tree house matched the description perfectly! The host was very responsive, the house was clean, and the temperature was comfortable. All instructions were provided prior to our arrival and easy to understand. The manager was friendly and we loved spending time with the animals. It was a little pricey but I would stay again. Great getaway for my husband and i to connect with nature!"
United States
Pattie
$294 nightly
The price is $333
Jul 21 - Jul 22
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
Smart TV

Serenity meets Taradise

Serenity meets Taradise
Union
$153 nightly
The price is $173
Jul 14 - Jul 15
Total with taxes and fees
Serenity meets Taradise
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.
$234 nightly
The price is $264
Jul 20 - Jul 21
Total with taxes and fees
Spacious, unique barn with beautiful views.
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.
$227 nightly
The price is $260
Jul 14 - Jul 15
Total with taxes and fees
Angel Sky Challenge
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
9.2 out of 10, Wonderful, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
$220 nightly
The price is $246
Jul 27 - Jul 28
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (36 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
$350 nightly
The price is $396
Jul 16 - Jul 17
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
$305 nightly
The price is $341
Jul 26 - Jul 27
Total with taxes and fees
Trainmaster's Inn - Caboose
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$164 nightly
The price is $183
Jul 20 - Jul 21
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Property grounds

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 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
$211 nightly
The price is $239
Aug 3 - Aug 4
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
$613 nightly
The price is $728
Jul 19 - Jul 20
Total with taxes and fees
6 Beds Home w/Game Room Perfect for Groups
Property grounds

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.8 out of 10, Exceptional, (17 reviews)
"The property was well kept, easy to get to, and close to where we needed to be."
United States
Dustin K.
$403 nightly
The price is $461
Jul 19 - Jul 20
Total with taxes and fees
Lakefront Cottage 2 Mi to Palladium in Worcester!
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
$208 nightly
The price is $210
Jul 15 - Jul 16
Total with taxes and fees
Cottage by the Castle – Downtown Spencer
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Apartment in town center #1

Apartment in town center #1
West Brookfield
8.8 out of 10, Excellent, (28 reviews)
"Stayed here to visit Treehouse brewing with some friends and it was perfect. "
United States
Chris G.
$300 nightly
The price is $335
Jul 15 - Jul 16
Total with taxes and fees
Apartment in town center #1
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

Comfort Inn & Suites Sturbridge - Brimfield

Comfort Inn & Suites Sturbridge - Brimfield

8/10 Good
"Quiet, good location. We had a great stay!"
Todd 10-night trip
Posted less than an hour ago
Comfort Inn & Suites Sturbridge - Brimfield

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 $108 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 in Dudley near TriState Speedway, or you can go with a secluded option if you want a relaxing stay. Dudley is known for its restaurants.

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

The Tree House at Underhill Hollow: Visitors like this Dudley vacation home rental. It offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a coffee maker, and kitchenware.

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 enjoy the outdoors, whereas family-friendly attractions include TriState Speedway. Dudley Hill Golf Club at Nichols College and Hiland Park 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.