Dering Harbor Chalets

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19
No exact matches found, but these alternatives could be just right

Recommended hotels in Dering Harbor

Exterior
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
8.0 out of 10, Very Good, (1008)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
$69 nightly
The price is $79
Dec 29 - Dec 30
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Motel in Old Saybrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
7.2 out of 10, Good, (463)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveler
$67 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Econo Lodge Inn & Suites Old Saybrook Westbrook
House on Chase Creek

Guesthouse in The Heights

House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
$104 nightly
The price is $119
Jan 6 - Jan 7, 2026
Total with taxes and fees
House on Chase Creek
Free self parking
Clinton Motel

Motel in Clinton

Clinton Motel
2.5 star property
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
$78 nightly
The price is $90
Dec 28 - Dec 29
Total with taxes and fees
Clinton Motel
Exterior
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
7.8 out of 10, Good, (1002)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
$101 nightly
The price is $116
Jan 1 - Jan 2, 2026
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
Exterior
Shorewood Inn

Motel in Riverhead

Shorewood Inn
2.5 star property
8.4 out of 10, Very Good, (710)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
$92 nightly
The price is $105
Dec 24 - Dec 25
Total with taxes and fees
Shorewood Inn
Exterior
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$171 nightly
The price is $193
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (548)
"Awesome stay!!! Great Location "
United States
Bryan
$174 nightly
The price is $198
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Harbor Front Inn
Exterior
Hamlet Inn

Motel in Southampton

Hamlet Inn
2.0 star property
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
$127 nightly
The price is $142
Dec 24 - Dec 25
Total with taxes and fees
Hamlet Inn
Front of property
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
9.4 out of 10, Exceptional, (231)
"Great stay, will definitely go again"
United States
ANTONIO J
$170 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Shoals Suites and Slips
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
9.6 out of 10, Exceptional, (404)
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
$126 nightly
The price is $144
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Bentley Hotel Southampton
Exterior
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.
$6,469 nightly
The price is $7,391
Jan 5 - Jan 6, 2026
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Exterior detail
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Very clean rustic cabin. The host was very accommodating. Fresh flowers and fruit were a nice touch from the host"
United States
Deb P.
$173 nightly
The price is $196
Jan 6 - Jan 7, 2026
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
7.2 out of 10, Good, (69)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
$121 nightly
The price is $138
Dec 26 - Dec 27
Total with taxes and fees
Hampton Bays Hotel on Main
Lunch, dinner, brunch served; American cuisine, beach views
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
8.6 out of 10, Excellent, (599)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$186 nightly
The price is $213
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sound View Greenport
Exterior
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
9.2 out of 10, Wonderful, (128)
"Great location. Nice and clean room and property"
United States
Eric
$128 nightly
The price is $147
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Niantic Inn
Front of property
Sea Haven Resort Motel

Motel in Southampton

Sea Haven Resort Motel
2.0 star property
7.8 out of 10, Good, (31)
"Great staff"
United States
Douglas
$134 nightly
The price is $153
Jan 17 - Jan 18, 2026
Total with taxes and fees
Sea Haven Resort Motel
Restaurant
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
$203 nightly
The price is $231
Dec 24 - Dec 25
Total with taxes and fees
Zey Hotel
Front of property
Liberty Inn

Liberty Inn

Liberty Inn
2.0 star property
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
$89 nightly
The price is $102
Dec 28 - Dec 29
Total with taxes and fees
Liberty Inn
Property grounds
Inn at Harbor Hill Marina

Bed & Breakfast in Niantic

Inn at Harbor Hill Marina
3.5 star property
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$159 nightly
The price is $183
Dec 29 - Dec 30
Total with taxes and fees
Inn at Harbor Hill Marina
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dering Harbor Hotel Reviews

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Room was beautiful and spacious. Staff was courteous and on point. "
Ron 2-night trip
Posted 16 hours ago
The Bentley Hotel Southampton

Find out more about Dering Harbor

Dering Harbor Chalets information

Number of reviews
7,408
Accommodation
1 Chalets
Lowest Price
$77
Highest Price
$7,391

Explore a world of travel with Expedia