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Dudley Vacation Rentals

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Dates

November 2026

December 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.

SAR 697 total

includes taxes & fees

12 Nov - 13 Nov

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.

SAR 675 total

includes taxes & fees

12 Nov - 13 Nov

A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

3. SteamPunk Bunk House and Intergalactic Way Station

Thompson

Pauline S.

SAR 679 total

includes taxes & fees

16 Nov - 17 Nov

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.

SAR 467 total

includes taxes & fees

12 Nov - 13 Nov

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.

SAR 1,381 total

includes taxes & fees

12 Nov - 13 Nov

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

6. 1 King Bed | Non-Smoking, Micfridge

Putnam

Anonymous traveler

SAR 378 total

includes taxes & fees

12 Nov - 13 Nov

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.

SAR 665 total

includes taxes & fees

12 Nov - 13 Nov

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.

SAR 1,195 total

includes taxes & fees

3 Dec - 4 Dec

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

SAR 434 total

includes taxes & fees

12 Nov - 13 Nov

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 traveler

SAR 1,790 total

includes taxes & fees

16 Nov - 17 Nov

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

11. Dove Cabin up in the Trees

Holland

Zachary C.

SAR 922 total

includes taxes & fees

12 Nov - 13 Nov

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.

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.

SAR 902 total

includes taxes & fees

12 Nov - 13 Nov

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

SAR 1,012 total

includes taxes & fees

22 Nov - 23 Nov

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 traveler

SAR 902 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

16. Cozy 1-bedroom cottage in serene Pomfret.

Pomfret

Aaron H.

SAR 992 total

includes taxes & fees

12 Nov - 13 Nov

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.

SAR 2,226 total

includes taxes & fees

12 Nov - 13 Nov

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

Worcester

Sierra M.

SAR 1,184 total

includes taxes & fees

12 Nov - 13 Nov

A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

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

Brimfield

Gregory C.

SAR 702 total

includes taxes & fees

12 Nov - 13 Nov

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.

SAR 1,355 total

includes taxes & fees

7 Dec - 8 Dec

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Find vacation rentals that suit your style

Top Dudley Hotel Reviews

An outdoor patio area with seating, tables, and decorative lights.

Wellsworth Hotel

Southbridge

10/10 Excellent

Brian

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

Holiday Inn Express & Suites Sturbridge by IHG

Sturbridge

10/10 Excellent

Tracy

A hotel with a covered patio, a stone fountain, and a brick pathway.

Comfort Inn & Suites Sturbridge - Brimfield

Sturbridge

10/10 Excellent

Jim

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

Scottish Inn Sturbridge

Sturbridge

10/10 Excellent

Dale

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

Suzanne

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

bernard

A Fairfield Inn & Suites by Marriott hotel with a covered entrance and landscaped surroundings.

Fairfield Inn & Suites by Marriott Worcester Auburn

Auburn

10/10 Excellent

Anonymous traveler

A hotel entrance with a covered walkway, a parking area, and a well-lit building facade.

Hampton Inn Auburn

Auburn

10/10 Excellent

A bunch of stuff in the surrounding area to eat and locations not to far away from many different places to do stuff. Everything was clean, staff was always nice. Free breakfast was simple but nice and had little something for everyone. The pools been down for a long time but for me personally not really a deal breaker. Simple clean room with a place to sleep while going out on daily adventures with the wife. Ive stayed in some really gross places traveling doing sports and other events so...

Adam

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

Super 8 by Wyndham Sturbridge

Sturbridge

10/10 Excellent

Anonymous traveler

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

Our first time at this location, we stayed here 2 nights while attending the May 2016 Brimfield markets. Easy on/off route 395 in a quiet area by an industrial park and rr tracks. About a 30 minute scenic drive to Brimfield (395N to 131 to 20). Although the hotel is 18 years old, the rooms were redone 2 years ago giving it a very modern appearance. The breakfast buffet was included (bacon, eggs, fresh fruit, yogart, oj, apple juice, great coffee, delicious blue berry waffles). Fresh baked...

peggy

A compact kitchen with a built-in refrigerator, a microwave, and a coffee machine.

Quiet Corner Inn

Brooklyn

10/10 Excellent

Anonymous traveler

A wooden interior with a dining table and chairs, a refrigerator, and shelves with glassware.

Trainmasters Inn

Palmer

10/10 Excellent

Anonymous traveler

A hotel room with two beds, a mural of a street scene, and a small table with a lamp.

Hamilton Inn

Sturbridge

10/10 Excellent

Anonymous traveler

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

Hampton Inn & Suites Worcester

Worcester

10/10 Excellent

Tammy

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

Wellsworth Hotel

10/10 Excellent

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?