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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Dudley Vacation Homes

The Tree House at Underhill Hollow
Exterior

The Tree House at Underhill Hollow

9.2 out of 10, Wonderful, (27)
"Great stay and the tree house was amazing. We loved walking the trails and finding all the fairy houses and interacting with the animals! "
The price is CA $150
CA $240 total
includes taxes & fees
Aug 25 - Aug 26
The Tree House at Underhill Hollow
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Fridge, microwave, oven, stovetop

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (16)
"Our stay at this property was great. Very clean and spacious. Area was very accessible to main roads. Our hosts were very responsive from booking through to the end of our stay. Will look to stay next time we visit Worcester "
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Spacious Home Near Mohegan Sun
Fridge, microwave, stovetop, coffee/tea maker

Spacious Home Near Mohegan Sun

2.0 out of 10, (1)
"My stay at this rental was deeply unsettling and unsafe. The apartment itself has a creepy, neglected vibe, and it only got worst. A serious safety issue occured when a teenager in our group fell through a rotted, unstable deck/ a terrifying and completely preventable accident. Even more concerning, the entrance code to our apartment was the same code used for all other units in the building. This made me feel extremely unsafe as anyone from another unit could have accessed ours at any time....
The price is CA $531
CA $1,122 total
includes taxes & fees
Sep 8 - Sep 9
Spacious Home Near Mohegan Sun
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Outdoor dining

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (110)
"It was a lovely cottage with beautiful views "
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Beautiful Lakefront Home with Private Beach
Lake

Beautiful Lakefront Home with Private Beach

9.2 out of 10, Wonderful, (173)
"Beautiful house and grounds! Very private with lots of room along with homey touches. Kids loved the toy cabinet and the pool table. Easy access to Boston. We thoroughly enjoyed our Easter weekend there! "
Beautiful Lakefront Home with Private Beach
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Exterior

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

9.8 out of 10, Exceptional, (10)
"Property is in excellent condition and well appointed. We enjoyed our stay."
The price is CA $439
CA $807 total
includes taxes & fees
Sep 15 - Sep 16
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Worcester Home on Indian Lake w/ Shared Boat Dock!
TV

Worcester Home on Indian Lake w/ Shared Boat Dock!

9.8 out of 10, Exceptional, (21)
"If you are looking for a great place to stay while in the Worcester area family this place will fill your need. The peaceful view on the lake is amazing."
Worcester Home on Indian Lake w/ Shared Boat Dock!
SteamPunk Bunk House and Intergalactic Way Station
Exterior

SteamPunk Bunk House and Intergalactic Way Station

10.0 out of 10, Exceptional, (9)
"This was a charming little apartment with a unique steam punk alien theme. If you have a playful mindset, I highly recommend staying at this location. I couldn’t have been more overjoyed with my stay."
The price is CA $150
CA $232 total
includes taxes & fees
Aug 25 - Aug 26
SteamPunk Bunk House and Intergalactic Way Station
3 Bed / 1.5 Bath Townhome
Fridge, microwave, oven, stovetop

3 Bed / 1.5 Bath Townhome

9.2 out of 10, Wonderful, (16)
"You will hear a little road noice but other then that it was perfect! Extremely clean and a great location. Highly recommend "
3 Bed / 1.5 Bath Townhome
Home Away from Home!
Smart TV, fireplace

Home Away from Home!

9.2 out of 10, Wonderful, (12)
"Lots of bedrooms with a great family gathering space. Quiet neighborhood. Would stay again at this property. Nicely decorated. "
The price is CA $258
CA $548 total
includes taxes & fees
Aug 25 - Aug 26
Home Away from Home!
Spacious, unique barn with beautiful views.
Interior

Spacious, unique barn with beautiful views.

10.0 out of 10, Exceptional, (1)
"This is a very unique and comfy place. Kids regretted that they only got to spend two nights here. I would mind spending more time hanging out in this place either myself! "
The price is CA $231
CA $367 total
includes taxes & fees
Aug 25 - Aug 26
Spacious, unique barn with beautiful views.
Amazing lake house with everything you need!
Dining

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (15)
"Look ing forward to booking again. Summer would be great to use the lake.Brad was very nice and easy to get ahold of. Loved this place!!!!"
Amazing lake house with everything you need!
Luxury Home, Pool, fireplace
Exterior

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (29)
"The property allowed for my extended family to gather under one roof and spend quality time together in a beautiful and quaint setting. "
Luxury Home, Pool, fireplace
Spacious 4-bedroom with four and half bathrooms
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (2)
"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."
The price is CA $382
CA $708 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 4-bedroom with four and half bathrooms
Charming 3-bed Lakehouse with Deck and Beach
Smart TV, fireplace

Charming 3-bed Lakehouse with Deck and Beach

10.0 out of 10, Exceptional, (11)
"The cottage was very clean, comfortable beds and beautiful setting. Perfect place for our flea market weekend."
Charming 3-bed Lakehouse with Deck and Beach
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

9.4 out of 10, Exceptional, (15)
"Highly recommend for a peaceful location that offers everything you need to feel at home. "
The price is CA $300
CA $559 total
includes taxes & fees
Sep 7 - Sep 8
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Lake House in Sturbridge w/All the Views!
Outdoor spa tub

Lake House in Sturbridge w/All the Views!

9.8 out of 10, Exceptional, (17)
"Loved the windows and light in the house. Quiet and peaceful. "
The price is CA $839
CA $1,644 total
includes taxes & fees
Aug 25 - Aug 26
Lake House in Sturbridge w/All the Views!
Spacious and luxurious 3-bedroom home w/jetted bathtub
Private kitchen

Spacious and luxurious 3-bedroom home w/jetted bathtub

9.2 out of 10, Wonderful, (5)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
Beautiful Renovated Townhome w/parking
Exterior detail

Beautiful Renovated Townhome w/parking

9.4 out of 10, Exceptional, (16)
"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "
Beautiful Renovated Townhome w/parking
Lakefront Getaway-Hot Tub + Kayaks + Paddleboards
Smart TV, fireplace, offices

Lakefront Getaway-Hot Tub + Kayaks + Paddleboards

2.0 star property
10.0 out of 10, Exceptional, (1)
"I truly can’t say enough good things about my stay. The house is exactly like the pictures but somehow even better in person. Everything was so clean and the check in/check out process was very easy. Sarah was so quick with communicating back and had the house stacked with everything you could imagine from plenty of pillows, blankets, tooth brushes etc. The views were beautiful and my dog loved how much space she had to herself. The neighbors are also so friendly and wave when you walk by! So...
Lakefront Getaway-Hot Tub + Kayaks + Paddleboards
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

Hampton Inn Auburn

Hampton Inn Auburn

10/10 Excellent
"For clean, spacious and pleasant overall."
Dwight 2-night trip
Posted 14 hours ago
Hampton Inn Auburn