Dudley Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Dudley

Exterior
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Holiday Home in Woodstock

9.8 out of 10, Exceptional, (75)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
The price is HK$2,034
HK$3,847 total
includes taxes & fees
3 Dec - 4 Dec
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Property grounds
Treehouse - Countryside - Farm Animals - Fire Pit

Cabin in Willington

9.4 out of 10, Exceptional, (28)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is HK$810
HK$2,052 total
includes taxes & fees
9 Dec - 10 Dec
Treehouse - Countryside - Farm Animals - Fire Pit
Exterior
Wizard's Roost at Underhill Hollow

Holiday Home in North Grosvenordale

9.6 out of 10, Exceptional, (20)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is HK$771
HK$1,221 total
includes taxes & fees
6 Dec - 7 Dec
Wizard's Roost at Underhill Hollow
Exterior
The Tree House at Underhill Hollow

Holiday Home in Thompson

9.4 out of 10, Exceptional, (34)
"We had a magical stay! Hosts were accommodating to our needs and eager to make our visit the best."
United States
Grahame E.
The price is HK$841
HK$1,346 total
includes taxes & fees
6 Dec - 7 Dec
The Tree House at Underhill Hollow
Terrace/patio
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Holiday Home in Sturbridge

9.8 out of 10, Exceptional, (89)
"Very Clean, great location"
United States
Anonymous traveller
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Exterior
Charming 2-bedroom apartment in welcoming Putnam

Apartment in Putnam

9.0 out of 10, Wonderful, (2)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is HK$645
HK$1,345 total
includes taxes & fees
15 Dec - 16 Dec
Charming 2-bedroom apartment in welcoming Putnam
Property grounds
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Cottage in Stafford

9.8 out of 10, Exceptional, (29)
"FANTASTIC STAY! there was an issue after arrival that was QUICKLY addressed... rest of stay was amazing! Beautiful home. Great kayaks.. lots of fishing!QUICK AND PLEASANT COMMUNICATIONS.THANK YOU!!!"
United States
Michelle O.
The price is HK$911
HK$2,400 total
includes taxes & fees
9 Dec - 10 Dec
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Interior
Bungalow 19 by the lake in Brimfield

Holiday Home in Brimfield

2.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, comfortable and great communication with host!"
United States
Elizabeth P.
Bungalow 19 by the lake in Brimfield
Dining
Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'

Cottage in Killingly

10.0 out of 10, Exceptional, (50)
"Our Family enjoyed staying in your lake house. We had an amazing experience. It felt like home."
United States
Lisa G.
Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'
Children’s area
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Holiday Home in Shrewsbury

9.6 out of 10, Exceptional, (32)
"I stayed at this property for almost a month and thoroughly enjoyed it. It had everything I needed and is conveniently located to Route 9 and I-435. The host was very responsive, which I greatly appreciated. It's nice to know such a comfortable place is available in Shrewsbury."
United States
Patty S.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Outdoor dining
Leicester Lake Front Home, Come Relax!

Holiday Home in Leicester

10.0 out of 10, Exceptional, (32)
"The home was lovely and the lakefront spot was beautiful! It was a very relaxing stay. "
United States
Erik S.
Leicester Lake Front Home, Come Relax!
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Holiday Home in West Brookfield

10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Interior
Cozy 2-Floor Apartment with Garage Access

Holiday Home in Main South

9.8 out of 10, Exceptional, (27)
"Overall great place, parking in garage was great! "
United States
Michell M.
Cozy 2-Floor Apartment with Garage Access
Exterior
SalsVista 2nd Floor Corner Apt

Apartment in Forest Grove

10.0 out of 10, Exceptional, (5)
"We very much enjoyed our weekend stay at this place. The apartment was immaculate and very comfortable."
United States
Anonymous traveller
SalsVista 2nd Floor Corner Apt
Fridge, microwave, oven, stovetop
Spacious 4-bedroom with four and half bathrooms

Holiday Home in Worcester

10.0 out of 10, Exceptional, (5)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is HK$2,141
HK$3,974 total
includes taxes & fees
3 Dec - 4 Dec
Spacious 4-bedroom with four and half bathrooms
Exterior
SteamPunk Bunk House and Intergalactic Way Station

Holiday Home in Thompson

10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$841
HK$1,302 total
includes taxes & fees
6 Dec - 7 Dec
SteamPunk Bunk House and Intergalactic Way Station
Fridge, microwave, oven, stovetop
Stunning Lakefront Escape! Book Your Dream Getaway!

Holiday Home in Woodstock

10.0 out of 10, Exceptional, (20)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
The price is HK$1,927
HK$3,709 total
includes taxes & fees
11 Dec - 12 Dec
Stunning Lakefront Escape! Book Your Dream Getaway!
Smart TV, fireplace
Home Away from Home!

Holiday Home in Worcester

9.4 out of 10, Exceptional, (14)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
The price is HK$1,448
HK$3,119 total
includes taxes & fees
7 Dec - 8 Dec
Home Away from Home!
Exterior
Spacious Massachusetts Apartment #2

Apartment in West Brookfield

9.0 out of 10, Wonderful, (29)
"We used both apartments for time with extended family. Nice to be in the same building."
United States
Tyler K.
The price is HK$623
HK$2,313 total
includes taxes & fees
3 Dec - 4 Dec
Spacious Massachusetts Apartment #2
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Holiday Home in Spencer

10.0 out of 10, Exceptional, (200)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dudley Hotel Reviews

Hampton Inn Sturbridge

Hampton Inn Sturbridge

10/10 Excellent
"Clean, decent breakfast. "
scott 1-night trip
Posted 2 days ago
Hampton Inn Sturbridge

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:

  • View our selection of featured holiday rentals in Dudley
  • Use the map to find apartments and other holiday homes in the Dudley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Dudley while they last

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

Frequently asked questions

Are there holiday rentals in Dudley?

Yes, there are holiday rentals in Dudley close to TriState Speedway, or you can select a more secluded option if you're looking for a relaxing stay. Dudley is known for its restaurants.

What are some of the best holiday rentals that Dudley has to offer?

Secluded 2-Acre Lakefront Home! Book Your Getaway!: This holiday home rental outside of Dudley is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Dudley?

Choose from 4 Expedia holiday rentals in Dudley for a memorable holiday.

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 Conant Library are other places to visit while you're in town.

What’s a holiday rental in Dudley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dudley. Holiday rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family getaway.