Dudley Vacation Rentals from CA $113: Short-Term Rentals for 2026

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Our top choices for Dudley vacation rentals

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. The Tree House at Underhill Hollow

Thompson

Zachary P.

CA $264 total

includes taxes & fees

Nov 10 - Nov 11

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. Wizard's Roost at Underhill Hollow

North Grosvenordale

Elizabeth G.

CA $256 total

includes taxes & fees

Nov 10 - Nov 11

A room with two wicker chairs and a small round table, a large window, and a red door.

3. SteamPunk Bunk House and Intergalactic Way Station

Thompson

Pauline S.

CA $256 total

includes taxes & fees

Nov 10 - Nov 11

A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Sturbridge

Lynn M. T.

CA $176 total

includes taxes & fees

Nov 10 - Nov 11

A bedroom with a wooden bed, large windows, and a view of greenery outside.

5. Rustic Farmette Studio with Hot Tub & Pool

Thompson

Lynn J.

CA $524 total

includes taxes & fees

Nov 10 - Nov 11

A modern interior with a dining area, kitchen, and seating space.

6. 1 King Bed | Non-Smoking, Micfridge

Putnam

Anonymous traveller

CA $142 total

includes taxes & fees

Nov 10 - Nov 11

A two-story house with a front porch, stone steps, and a driveway.

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

Putnam

Dan M.

CA $281 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

8. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Sturbridge

Trish N.

CA $448 total

includes taxes & fees

Nov 30 - Dec 1

A living room with a TV, a sofa, a chair, a lamp, and a window with sheer curtains.

9. Clean & Cozy Private room - 3 floor_R 1

Union HIll

CA $163 total

includes taxes & fees

Nov 10 - Nov 11

A lakeside cabin with a deck, a dock, and a small docked boat.

10. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Sturbridge

Anonymous traveller

CA $674 total

includes taxes & fees

Nov 10 - Nov 11

A wooden cabin with a glass upper floor, surrounded by a forest.

11. Dove Cabin up in the Trees

Holland

Zachary C.

CA $350 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

12. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Stafford

Lisa S.

CA $426 total

includes taxes & fees

Nov 11 - Nov 12

A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

13. Large 3BD 1st Floor Apartment Minutes from 290

Franklin Plantation

Taisha M.

CA $440 total

includes taxes & fees

Nov 10 - Nov 11

A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Willington

Stacy

CA $319 total

includes taxes & fees

Nov 17 - Nov 18

A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

15. Newly Refreshed 3bd Spacious Unit Minutes from 290

Franklin Plantation

Anonymous traveller

CA $454 total

includes taxes & fees

Nov 12 - Nov 13

A house with a white porch, a black door, and a window with a white frame.

16. Cozy 1-bedroom cottage in serene Pomfret.

Pomfret

Aaron H.

CA $376 total

includes taxes & fees

Nov 10 - Nov 11

A dining area with a high ceiling, skylights, and a view of the outdoors.

17. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock

Emma S.

CA $873 total

includes taxes & fees

Nov 10 - Nov 11

18. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Worcester

Sierra M.

CA $486 total

includes taxes & fees

Nov 10 - Nov 11

A round metal fire pit with grilling tools and a red chair in the background.

19. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Brimfield

Gregory C.

CA $308 total

includes taxes & fees

Nov 15 - Nov 16

A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

20. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Main South

"Rented the property to attend a series of events at Clark University. Literally walking distance to the school so it was quite convenient. Apartment was clean, beds were comfortable. Being able to park three cars in the driveway was a huge plus as street parking near the apartment was extremely challenging. Being a Clark alum, was quite familiar with the neighborhood so I knew what to expect. Felt completely safe in the apartment as every door to the hallways had sufficient locks. We did blow a...

Elyse D.

CA $439 total

includes taxes & fees

Dec 1 - Dec 2

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Find vacation rentals that suit your style

Top Dudley Hotel Reviews

A hotel entrance with a covered walkway, columns, and a brick facade.

Holiday Inn Express & Suites Sturbridge by IHG

Sturbridge

10/10 Excellent

Tyler

A white colonial-style house with a symmetrical facade, a central entrance, and a well-maintained garden with colorful flowers.

Publick House Historic Inn and Country Motor Lodge

Sturbridge

10/10 Excellent

John

A large building with multiple windows and a well-maintained garden with various plants and flowers.

Scottish Inn Sturbridge

Sturbridge

10/10 Excellent

Fr. Toby

A hotel with a parking lot, a covered entrance, and a brick facade.

Holiday Inn Express Hotel & Suites Auburn by IHG

Auburn

10/10 Excellent

Bill

A modern lounge area with a stone wall, a fireplace, and a seating arrangement including sofas and a coffee table.

Homewood Suites By Hilton Worcester

Worcester Central Business District

10/10 Excellent

Julia

La Quinta Inn by Wyndham Auburn Worcester

Auburn

8/10 Good

Joel

A Comfort Inn & Suites hotel with a well-maintained garden and a clear view of the building's entrance.

Comfort Inn & Suites Dayville - Killingly Industrial Park

Dayville

10/10 Excellent

Ron

A pool with a wooden deck and railing, overlooking a lake with boats.

Super 8 by Wyndham Sturbridge

Sturbridge

10/10 Excellent

J.

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

Hampton Inn & Suites Worcester

Worcester

10/10 Excellent

Jonathan

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dudley vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dudley vacation rentals we have selected for you start as low as CA $113 per night. Entering your travel dates in the search wizard 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.

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.

Dudley Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Dudley vacation rentals

1. The Tree House at Underhill Hollow

2. Wizard's Roost at Underhill Hollow

3. SteamPunk Bunk House and Intergalactic Way Station

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

5. Rustic Farmette Studio with Hot Tub & Pool

6. 1 King Bed | Non-Smoking, Micfridge

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

8. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

9. Clean & Cozy Private room - 3 floor_R 1

10. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

11. Dove Cabin up in the Trees

12. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

13. Large 3BD 1st Floor Apartment Minutes from 290

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

15. Newly Refreshed 3bd Spacious Unit Minutes from 290

16. Cozy 1-bedroom cottage in serene Pomfret.

17. Secluded 2-Acre Lakefront Home! Book Your Getaway!

18. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

19. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

20. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Find vacation rentals that suit your style

Top Dudley Hotel Reviews

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent

Find out more about Dudley

Dudley vacation rentals: An excellent choice for every season

How to find incredible deals on Dudley rentals

Frequently Asked Questions

Are there vacation rentals in Dudley?

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

How many vacation rentals are there in Dudley?

What’s there to see and do in Dudley?

What’s a vacation rental in Dudley like?