Search Vacation Homes in Dering Harbor

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Dering Harbor vacation homes

Smart TV, fireplace, table tennis, books
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Vacation Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,353 nightly
The price is $7,259
Dec 15 - Dec 16
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Smart TV, books
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (4)
"Communication was excellent. "
United States
Katy C.
$356 nightly
The price is $403
Jan 5 - Jan 6, 2026
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
9.0 out of 10, Wonderful, (4)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
$323 nightly
The price is $365
Dec 15 - Dec 16
Total with taxes and fees
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Dining
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins

Vacation Home in Clinton

LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
2.0 star property
10.0 out of 10, Exceptional, (3)
"Vincent was amazing to work with! We decided to change the dates and he was very patient and helpful while we got it updated with VRBO. The home is in a peaceful neighborhood with beautiful trees and active squirrels (my daughter’s favorite part). The location was convenient for our needs. We all enjoyed the game tables and the convenience of the washer and dryer. We even tried out the projector one night to watch a couple of episodes of Gilmore Girls – so fun! Vincent checked in once we arrived...
United States
Erin S.
$451 nightly
The price is $510
Dec 14 - Dec 15
Total with taxes and fees
LONG-TERM Relaxing Glass House - Fall Leaves/Beach 5mins/Ski 25mins
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
$453 nightly
The price is $513
Dec 16 - Dec 17
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
$771 nightly
The price is $881
Dec 16 - Dec 17
Total with taxes and fees
Blackberry: Private home with jacuzzi year-round
Smart TV, fireplace
Spacious 5-bedroom house with water views and 2 houses from the bay.

Vacation Home in Sag Harbor

Spacious 5-bedroom house with water views and 2 houses from the bay.
$5,630 nightly
The price is $6,432
Dec 17 - Dec 18
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.
Interior
Adorable Cottage, 5 min walk to water & town

Vacation Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town
9.4 out of 10, Exceptional, (14)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$368 nightly
The price is $416
Dec 14 - Dec 15
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town
Property grounds
Stylish Modern Stay Steps from the Ocean

Vacation Home in Clinton

Stylish Modern Stay Steps from the Ocean
10.0 out of 10, Exceptional, (1)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
$298 nightly
The price is $337
Dec 14 - Dec 15
Total with taxes and fees
Stylish Modern Stay Steps from the Ocean
Terrace/patio
American Beech in Greenport - Petite King Room 7

Vacation Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$242 nightly
The price is $277
Dec 14 - Dec 15
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Outdoor dining
Coastal New England Waterfront Home, Harkness Park, Casinos

Vacation Home in Waterford

Coastal New England Waterfront Home, Harkness Park, Casinos
10.0 out of 10, Exceptional, (126)
"Wonderful location (very close to downtown Niantic); clean, bright, beautiful home; well appointed kitchen overall; loved gate at top of stairs, rail for bottom bunk and high chair since I have a toddler; owner was very responsive, kind and helpful when needed. I would definitely recommend and stay again!"
United States
Anne M.
$548 nightly
The price is $620
Dec 14 - Dec 15
Total with taxes and fees
Coastal New England Waterfront Home, Harkness Park, Casinos
Interior
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR

Vacation Home in Clinton

House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR
2.0 star property
$182 nightly
The price is $206
Dec 14 - Dec 15
Total with taxes and fees
House in Clinton, CT - Tide Unit - Charming Furnished Boutique 1BR
Interior
Sag Harbor Water View w Dock 1.5ml from town

Vacation Home in Bay Point

Sag Harbor Water View w Dock 1.5ml from town
$5,589 nightly
The price is $6,385
Dec 16 - Dec 17
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town
Interior
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Vacation Home in Saybrook Manor

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
9.6 out of 10, Exceptional, (133)
"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "
United States
Rob C.
$510 nightly
The price is $578
Dec 14 - Dec 15
Total with taxes and fees
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Dining
Charming Northfork Townhouse- walk to all

Vacation Home in Greenport

Charming Northfork Townhouse- walk to all
10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
$583 nightly
The price is $666
Dec 14 - Dec 15
Total with taxes and fees
Charming Northfork Townhouse- walk to all
Property grounds
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Vacation Home in Southampton

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
10.0 out of 10, Exceptional, (15)
"Just finished a 5 day stay. Best house rental ever! Great and thoughtful hosts. Super relaxing and extremely luxurious! Highly recommend!"
United States
William H.
$1,504 nightly
The price is $1,593
Jan 5 - Jan 6, 2026
Total with taxes and fees
Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Dining
Immaculate Waterfront 2 bedroom!

Vacation Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$547 nightly
The price is $625
Dec 14 - Dec 15
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Interior
Upscale Hamptons Home: 1 Mi to Sammys Beach!

Vacation Home in East Hampton

Upscale Hamptons Home: 1 Mi to Sammys Beach!
9.4 out of 10, Exceptional, (3)
"Wonderful property. Lisette was a fantastic host and her home updated and modern. "
United States
Joanna D.
$1,085 nightly
The price is $1,240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Upscale Hamptons Home: 1 Mi to Sammys Beach!
Dining
Designer East Hampton Farmhouse

Vacation Home in East Hampton North

Designer East Hampton Farmhouse
$1,057 nightly
The price is $1,127
Jan 2 - Jan 3, 2026
Total with taxes and fees
Designer East Hampton Farmhouse
TV, fireplace, stereo, offices
Serene East Hampton Escape

Vacation Home in East Hampton North

Serene East Hampton Escape
2.0 star property
$1,001 nightly
The price is $1,065
Jan 2 - Jan 3, 2026
Total with taxes and fees
Serene East Hampton Escape
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 Dering Harbor Hotel Reviews

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Great overall service."
Richard T 3-night trip
Posted 8 hours ago
Madison Beach Hotel

Find out more about Dering Harbor

Dering Harbor Vacation Homes information

Number of reviews
248
Accommodation
1569 Vacation Homes
Lowest Price
$277
Highest Price
$7,259

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