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Compare 77 Vacation Homes in Dudley with updated reviews, rates, and availability.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Property grounds

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (180)
"Overall a wonderful stay. This is a duplex and the owner lives next door. Nice neighborhood and beautiful view"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Welcome to family fun and dining, directly on the lake!

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

9.8 out of 10, Exceptional, (102)
"Very nice, well equipped, absolutely beautiful view!!!!!!"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Room

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.6 out of 10, Exceptional, (19)
"Great "
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Large relaxing house in 25 acres of private woods with lake access.
Dining

Large relaxing house in 25 acres of private woods with lake access.

10.0 out of 10, Exceptional, (16)
"Excellent home in the woods. All as advertised, my family and I thoroughly enjoyed it. Communication with the owner was excellent. 10/10, we’ll be back next time we’re in the area"
Large relaxing house in 25 acres of private woods with lake access.
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms
Exterior

Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms

10.0 out of 10, Exceptional, (1)
"Everything was spotlessly clean. The beds were comfortable, and every convenience was considered. Excellent place for a larger group—we needed 4 bedrooms—coming to town to move my son in to WPI for college. Would strongly recommend!!!"
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Interior

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (29)
"This was an amazing property! My mother stayed there and said it was cozy and she felt at home. The place was clean, cozy, and quaint! Would definitely stay there again!"
The price is AED 419
AED 886 total
includes taxes & fees
27 Nov - 28 Nov
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
The Tree House at Underhill Hollow
Exterior

The Tree House at Underhill Hollow

9.4 out of 10, Exceptional, (13)
"Michael has done a fantastic job not only providing a comfortable and beautiful accommodation, but his creativity and skill shine in the many wonderful contraptions, puzzles and surprises around the property. A great place to stay for the gorgeous CT scenery, even better for the many opportunities of adventure scattered around the grounds. Will definitely recommend this to friends and family, and hope to come back in the future to find anything we missed!"
The price is AED 441
AED 686 total
includes taxes & fees
26 Nov - 27 Nov
The Tree House at Underhill Hollow
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
Exterior

Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

10.0 out of 10, Exceptional, (9)
"Beautifully appointed home on a beautiful lake in Woodstock, CT. We enjoyed kayaking on the lake, visiting nearby orchards and hiking the many scenic trails nearby. Many great restaurants in the area as well. Although we did not partake, there is a great rail trail nearby for hiking, walking, etc. The home listing is very accurate, the kitchen is well equipped, and the cleanliness of the home is top notch. In addition, the hosts Heather and Dan, were very responsive and were...
The price is AED 1,010
AED 1,888 total
includes taxes & fees
1 Dec - 2 Dec
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
Cozy bedrooms in Shrewsbury warm town and convenient
Room

Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

10.0 out of 10, Exceptional, (5)
"Very comfortable 3 bedroom house. Great location."
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly
Charming 3 bedroom home Centrally located in Worcester
Living area

Charming 3 bedroom home Centrally located in Worcester

9.0 out of 10, Wonderful, (2)
"The home is very comfortable and good neighborhood.Bed was comfy and beding too.Would return again!"
Charming 3 bedroom home Centrally located in Worcester
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
Exterior

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

9.8 out of 10, Exceptional, (60)
"This property is amazing! We had such a great weekend - the water view is incredible and we had everything we needed for a cozy stay. Thank you!!"
The price is AED 1,010
AED 1,877 total
includes taxes & fees
2 Dec - 3 Dec
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
Wizard's Roost at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

10.0 out of 10, Exceptional, (5)
"Cute and fun spot in the country. Very quiet. Room was clean and had everything we needed. Beds comfy. Nice property. Very friendly owner. A bit dark at the top of the driveway if you come in at night watch for the turn. "
The price is AED 404
AED 623 total
includes taxes & fees
27 Nov - 28 Nov
Wizard's Roost at Underhill Hollow
Spacious and luxurious 3-bedroom home w/jetted bathtub
Interior

Spacious and luxurious 3-bedroom home w/jetted bathtub

10.0 out of 10, Exceptional, (3)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
Lake House in Sturbridge w/All the Views!
House from above the lake

Lake House in Sturbridge w/All the Views!

9.8 out of 10, Exceptional, (6)
"We had a great time in Sturbridge. Can't beat the location of this house - it's absolutely beautiful, and very close to Old Sturbridge Village and a cute coffee shop we frequented during the long weekend. Everything was nice and clean, the hot tub was great, and it was easy to check in. The beds are comfortable and it was nice to not have to worry about the linens upon checkout. The host replied super promptly when we had questions about the location of trash/recycling bins, and when there was...
The price is AED 2,443
AED 4,034 total
includes taxes & fees
30 Nov - 1 Dec
Lake House in Sturbridge w/All the Views!
Full family home 200 ft from the lake shore. Dog friendly!
Exterior

Full family home 200 ft from the lake shore. Dog friendly!

10.0 out of 10, Exceptional, (5)
"Great location for our family visit. Property was very clean. Host very responsive. The beautiful sunrises over the lake were an additional bonus!"
The price is AED 1,121
AED 2,136 total
includes taxes & fees
8 Dec - 9 Dec
Full family home 200 ft from the lake shore. Dog friendly!
Full House/Heart of Worcester
Exterior detail

Full House/Heart of Worcester

The price is AED 533
AED 1,299 total
includes taxes & fees
2 Dec - 3 Dec
Full House/Heart of Worcester
Spacious luxury 3 bedroom apartment
living room with huge TV

Spacious luxury 3 bedroom apartment

8.0 out of 10, Very Good, (2)
"Came from out of town with friends to enjoy a music festival at the Palladium. Location was easy to find and accesible to shops/food. Apartment was easy to access around back side. In our case we walked up the driveway as the gate was locked. Safe second floor apartment. Bed were clean, and rooms spacious. Only thing that was inconvenient the missing handle from the freezer door. "
Spacious luxury 3 bedroom apartment
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
Exterior

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

10.0 out of 10, Exceptional, (49)
"5 of us stayed here for a week while we were at an event nearby. The place is gorgeous, huge, impecably clean, and for our purposes very convenient. We particularly appreciated the nice touches of a bottle of wine and some snacks, and the large and very functional washing machine/dryer setup, We’re immediately trying to rebook for a trip next year!. We met the host once during our stay and they delightfully gave us a tour and he made sure everything was going well. Lovely to have a VRBO...
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
"Duck Rock" Lakefront House with 200' Private Waterfront
Sunset View from Large Screened Deck

"Duck Rock" Lakefront House with 200' Private Waterfront

10.0 out of 10, Exceptional, (15)
"Loved the house"
"Duck Rock" Lakefront House with 200' Private Waterfront
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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Other property types in Dudley

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Interior

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (29)
"This was an amazing property! My mother stayed there and said it was cozy and she felt at home. The place was clean, cozy, and quaint! Would definitely stay there again!"
The price is AED 419
AED 886 total
includes taxes & fees
27 Nov - 28 Nov
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
Exterior

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

9.8 out of 10, Exceptional, (60)
"This property is amazing! We had such a great weekend - the water view is incredible and we had everything we needed for a cozy stay. Thank you!!"
The price is AED 1,010
AED 1,877 total
includes taxes & fees
2 Dec - 3 Dec
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
Treehouse | Countryside | Farm Animals | Fire Pit
Treehouse in Connecticut

Treehouse | Countryside | Farm Animals | Fire Pit

9.6 out of 10, Exceptional, (21)
"My second time here and it honestly feels like a second home. The animals are friendly and so was Carmen! It's honestly a must, if you have a bucket list. Joseph was very helpful and thorough as a superhost. I highly recommend visiting! "
The price is AED 470
AED 1,065 total
includes taxes & fees
2 Dec - 3 Dec
Treehouse | Countryside | Farm Animals | Fire Pit
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.