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Dudley Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Dudley holiday rentals

Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
The price is HK$1,377
HK$2,019 total
includes taxes & fees
6 Jul - 7 Jul
Dove Cabin up in the Trees
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 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.
The price is HK$988
HK$1,474 total
includes taxes & fees
9 Jul - 10 Jul
Wizard's Roost at Underhill Hollow
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.
The price is HK$988
HK$1,519 total
includes taxes & fees
9 Jul - 10 Jul
The Tree House at Underhill Hollow
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.
The price is HK$1,306
HK$2,075 total
includes taxes & fees
6 Jul - 7 Jul
Spacious, unique barn with beautiful views.
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
9.4 out of 10, Exceptional, (6 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
The price is HK$1,271
HK$1,603 total
includes taxes & fees
6 Jul - 7 Jul
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.6 out of 10, Excellent, (4 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.
The price is HK$1,130
HK$1,946 total
includes taxes & fees
7 Jul - 8 Jul
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.0 out of 10, Wonderful, (34 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
The price is HK$2,765
HK$4,536 total
includes taxes & fees
14 Jul - 15 Jul
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
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.
The price is HK$1,436
HK$1,635 total
includes taxes & fees
5 Jul - 6 Jul
Cottage by the Castle – Downtown Spencer
TV

Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (3 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is HK$941
HK$2,182 total
includes taxes & fees
5 Jul - 6 Jul
Large 3BD 1st Floor Apartment Minutes from 290
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
The price is HK$2,157
HK$4,030 total
includes taxes & fees
13 Jul - 14 Jul
Spacious 4-bedroom with four and half bathrooms
Smart TV, books

Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
The price is HK$1,906
HK$2,487 total
includes taxes & fees
6 Jul - 7 Jul
Heart of Shrewsbury St – 2BR Stay
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, (41 reviews)
"Very nice area."
United States
maureen p.
The price is HK$1,176
HK$2,763 total
includes taxes & fees
15 Jul - 16 Jul
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is HK$3,529
HK$5,798 total
includes taxes & fees
13 Jul - 14 Jul
Stunning Lakefront Escape! Book Your Dream Getaway!
Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
Lakefront Cottage 2 Mi to Palladium in Worcester!
Dining

12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
9.4 out of 10, Exceptional, (3 reviews)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is HK$2,079
HK$3,880 total
includes taxes & fees
5 Jul - 6 Jul
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (2 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.
The price is HK$1,365
HK$2,707 total
includes taxes & fees
9 Jul - 10 Jul
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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
The price is HK$1,115
HK$2,428 total
includes taxes & fees
7 Jul - 8 Jul
Treehouse - Countryside - Farm Animals - Fire Pit
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.
The price is HK$1,176
HK$2,716 total
includes taxes & fees
5 Jul - 6 Jul
Trainmaster's Inn - Caboose
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)
The price is HK$988
HK$1,474 total
includes taxes & fees
9 Jul - 10 Jul
SteamPunk Bunk House and Intergalactic Way Station
Exterior

The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (32 reviews)
"Loved the carriage house and nicely decorated with all the artwork! I wish we could have stayed longer. If I need a place to stay in the area, I will definitely be staying there!"
United States
Patti G.
The Carriage House at Chaprae Hall
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

Holiday Inn Express Hotel & Suites Auburn by IHG

Holiday Inn Express Hotel & Suites Auburn by IHG

10/10 Excellent
"Good service"
Isaacmoise 1-night trip
Posted 1 hour ago
Holiday Inn Express Hotel & Suites Auburn by IHG

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:

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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?

3-bedroom house on Webster Lake with amazing views, beach and boat launch access: This holiday home rental outside of Dudley is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Dudley?

Choose from 3 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.