Title: Dering Harbor Vacation Home Rentals from CA $342: Search Top Private Vacation Homes for Rent | Expedia.ca

[Dering Harbor Travel Guide](https://expedia.ca/Dering-Harbor.dx553248634998885605)[Hotels in Dering Harbor](https://expedia.ca/Dering-Harbor-Hotels.d553248634998885605.Travel-Guide-Hotels)[Vacation Rentals in Dering Harbor](https://expedia.ca/Dering-Harbor-Vacation-Rentals.d553248634998885605.Travel-Guide-VacationRentals)[Dering Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Dering-Harbor.d553248634998885605.Car-Rental-Guide)[Dering Harbor Vacation Packages](https://expedia.ca/Dering-Harbor.d553248634998885605.Destination-Travel-Guides)

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# Dering Harbor Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248634998885605&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Dering Harbor vacation homes

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/3368cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/98c458f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Water Mill

[](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information)

10/10

Exceptional

(6)

"Highly recommend everything from start to finish went smoothly and it was a great experience!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie M.

CA $5,939

CA $10,417 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/f7b0c3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/4ed75f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/8aa6190f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0c0a866f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Lyme

[](https://www.expedia.ca/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

10/10

Exceptional

(5)

"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hemie J.

CA $119

CA $556 total

includes taxes & fees

Jan 20 - Jan 21, 2026

[](https://www.expedia.ca/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/32bb5853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3a7a158a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Lyme

[](https://www.expedia.ca/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah G.

CA $162

CA $504 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/f6c15885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/aeb85212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/d416d8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sag Harbor

[](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information)

CA $5,521

CA $8,897 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/a0e54ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/623abb73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westbrook

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

10/10

Exceptional

(1)

"Perfect house for 6 guests. Loved that it was close to the beach."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shannon G.

CA $202

CA $710 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Hampton

[](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Suzanne R.

CA $137

CA $1,260 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/f20bc122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/00b024ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/4bd4eab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampton Bays

[](https://www.expedia.ca/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

9.6/10

Exceptional

(14)

"Nice house. Photos and descriptions represent it very accurately. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Will K.

CA $207

CA $1,757 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Hampton-Bays-Hotels-Black-Swan-Beachfront-Home-W-Year-Round-Jacuzzi.h92502496.Hotel-Information)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/7a209baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/f8c8a8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/d26d882e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/8f1986e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bay Point

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information)

CA $6,211

CA $8,824 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e500d985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

[](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

9.0/10

Wonderful

(4)

"We thoroughly enjoyed our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Parent From The Heart, Inc. E.

CA $219

CA $342 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/8c60ece7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/00ea4ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/f4c65ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly Z.

CA $248

CA $498 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/bcef6dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/w1330h900x18y0-56561db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/4f11d273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/b4081022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Hampton North

[](https://www.expedia.ca/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information)

CA $399

CA $1,194 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/55e69dfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/df4a82cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/d0d2900f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/51000000/50610000/50607400/50607334/bce95391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southampton

[](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information)

10/10

Exceptional

(15)

"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deborah V.

CA $1,575

CA $2,198 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Southampton-Hotels-Contemporary-Southampton-Village-Home-Walking-Distance-To-Town.h50607334.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h953x0y0-69414cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/a2326e66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Saybrook Manor

[](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

9.6/10

Exceptional

(133)

"We loved our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deana L.

CA $345

CA $798 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/c014f457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/41720b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/3f2d6f0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323362/w1836h1206x4y0-8abfec0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Hampton

[](https://www.expedia.ca/East-Hampton-Hotels-NEW-Upscale-Hamptons-Home-1-Mi-To-Sammys-Beach.h78323362.Hotel-Information)

9.4/10

Exceptional

(3)

"Wonderful property. Lisette was a fantastic host and her home updated and modern. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joanna D.

CA $966

CA $1,711 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/East-Hampton-Hotels-NEW-Upscale-Hamptons-Home-1-Mi-To-Sammys-Beach.h78323362.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/99132894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/4c3022eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/f0c859fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/d9a3174d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Coastal-New-England-Waterfront-Home.h23144923.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anne M.

CA $393

CA $776 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Waterford-Hotels-Coastal-New-England-Waterfront-Home.h23144923.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/bb644073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/ee30d2e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/4bd3774d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74200000/74196800/74196767/6a96971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

[](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

9.6/10

Exceptional

(9)

"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Laura B.

CA $371

CA $771 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse.h74196767.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/w1035h701x17y0-8bcaee6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/30220c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/7251e4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74210000/74202200/74202120/680aee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

[](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Beth R.

CA $462

CA $929 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Greenport-Hotels-Greenport-Village-Townhouse-Walk-To-Town.h74202120.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/b8434d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/305503f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/02a1d23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/e51e1447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampton Bays

[](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information)

10/10

Exceptional

(5)

"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael L.

CA $449

CA $886 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games, printers](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/30fcbecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

[](https://www.expedia.ca/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information)

10/10

Exceptional

(3)

"good experience"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $828

CA $1,621 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Southold-Hotels-Beautifully-Farmhouse.h113098265.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/ebb70869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/c4e80e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/7ee4af6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/f9e71e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southampton

[](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information)

9.0/10

Wonderful

(10)

"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Panagiota K.

CA $453

CA $1,114 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-01-04&endDate=2026-01-05&regionId=553248634998885605&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Dering+Harbor%2C+New+York%2C+United+States+of+America&regionId=553248634998885605&latLong=41.092876%2C-72.346748&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Dering+Harbor%2C+New+York%2C+United+States+of+America&regionId=553248634998885605&latLong=41.092876%2C-72.346748&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Dering+Harbor%2C+New+York%2C+United+States+of+America&regionId=553248634998885605&latLong=41.092876%2C-72.346748&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Dering+Harbor%2C+New+York%2C+United+States+of+America&regionId=553248634998885605&latLong=41.092876%2C-72.346748&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Dering+Harbor%2C+New+York%2C+United+States+of+America&regionId=553248634998885605&latLong=41.092876%2C-72.346748&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=VACATION_HOME)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Dering+Harbor%2C+New+York%2C+United+States+of+America&regionId=553248634998885605&latLong=41.092876%2C-72.346748&adults=2&startDate=2026-03-21&d1=2026-03-21&endDate=2026-03-24&d2=2026-03-24&lodging=HOUSE_BOAT)

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## Top Dering Harbor Hotel Reviews

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Room was clean though a bit rustic. Staff was very nice. No housekeeping but was able to collect all clean towels, etc. in the office. We were here for a funeral. Pier Blue Inn was close to funeral home, Catholic Church, and repast. Nice restaurants so close by! I’m glad I booked this place. Added a second night to avoid Friday night traffic back to our house in Rockland County NY."

[](https://expedia.ca/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf_y.jpg)

### Sag Harbor Inn

10/10 Excellent

"love this Inn, it is very welcoming, a bit old school, which we love! Room is large , parking free and easy, and we love the breakfast room and all day coffee."

[](https://expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing "

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg)

### Hamlet Inn

10/10 Excellent

"Lovely experience! Just wish we could have been able to stay longer. Clean room, kind, helpful staff. We're coming back!"

[](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"The staff was friendly. The room was good. "

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![The Niantic Inn](https://images.trvl-media.com/lodging/16000000/15010000/15001900/15001889/da242095_y.jpg)

### The Niantic Inn

10/10 Excellent

"There was plenty of parking during my stay. The room was clean & welcoming. Will definitely be back. "

[](https://expedia.ca/Niantic-Hotels-The-Niantic-Inn.h15001889.Hotel-Information)

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Friendly and helpful staff, wonderful dining experience at Fresh Salt"

[](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![Sea Crest Resort](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg)

### Sea Crest Resort

10/10 Excellent

"Lovely, clean 1 bedroom with spectacular view"

[](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information)

![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg)

### Madison Beach Hotel

10/10 Excellent

"beautiful room and views"

[](https://expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information)

## Find out more about Dering Harbor

## Dering Harbor Vacation Homes information

| Number of reviews | 270                 |
| ----------------- | ------------------- |
| Accommodation     | 1569 Vacation Homes |
| Lowest Price      | CA $342             |
| Highest Price     | CA $10,417          |

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- [Flights to Greenport ](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
- [Flights to Shelter Island ](https://www.expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)
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- [Flights from Orient ](https://www.expedia.ca/lp/flights/6326191/flights-from-orient)
- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Visit East Marion ](https://www.expedia.ca/East-Marion.dx6069914)
- [Visit Pipes Cove ](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
- [Kontokosta Winery ](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [Orient Vacations ](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)
- [Visit Shelter Island ](https://www.expedia.ca/Shelter-Island.dx157359)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
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- [Shelter Island Vacation Rentals ](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)

- [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Shelter Island Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)
- [Things to do in Shelter Island ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

- [Book Vacation Homes in Dering Harbor on Expedia.com ](https://www.expedia.com/Dering-Harbor-Private-Vacation-Homes.d553248634998885605-aaPrivateVacationHomes.Travel-Guide-Accommodation)