Holiday homes by the sea in Southold
Choose the right place for you
FACILITIES
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Pets Allowed
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Wi-Fi
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Non Smoking Only
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
DISTANCE FROM CENTRE
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Less than 1 km
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Less than 3 km
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Less than 5 km
Holiday rental deals in Southold
We have selected the best holiday accommodation by the sea in Southold. Bluepillow allows you to save money, by finding the best rates on the main vacation rental websites in Southold
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Southold - United States
North Fork Guest House
- Hotel
13.1 Exceptional (30)When you stay at North Fork Guest House in Cutchogue, you'll be near the beach, just steps from Bedell Cellars and 7 minutes by foot from Pindar Vineyards. This bed & breakfast is 0.6 mi (1 km) from Lenz ... -
Southold - United States
The Cliffside Resort Condominiums
- Hotel
11.4 Exceptional (634)With beautiful views of the sunsets over Long Island Sound, this Greenport resort features spacious grounds and a private beach. Free Wi-Fi is available in all areas. ... -
Southold - United States
Fordham House
- Hotel
13.3 Exceptional (48)Located in Greenport, Fordham House is near the beach, within a 5-minute walk of Eastern Long Island Hospital and Stony Brook Eastern Long Island Hospital. This bed & breakfast is 0.5 mi (0.9 km) from ... -
Southold - United States
The Farmhouse Bed and Breakfast
- Hotel
13.3 Exceptional (15)When you stay at The Farmhouse Bed and Breakfast in Cutchogue, you'll be near the beach, within a 5-minute drive of Peconic Bay Winery and Castello di Borghese / Hargrave Vineyard. This bed & breakfast ... -
Southold - United States
Peconic Sound Beach Home: Backyard & Vineyards
- 7 Guests 3Bedrooms
13.1 Exceptional (18)Offering sea views, Peconic Sound Beach Home: Backyard & Vineyards is an accommodation located in Peconic, a few steps from Goldsmith's Inlet Park and 31 km from Splish Splash. ... -
Southold - United States
Victorian Seasons Stirling
- Hotel
With a stay at Victorian Seasons Stirling in Greenport, you'll be near the beach, within a 15-minute walk of Kontokosta Winery and Greenport Farmers' Market. This beach guesthouse is 1 mi (1.6 km) from ... -
Southold - United States
Charming Greenport Gem 1, 1 Mile to Ferry!
- 6 Guests 2Bedrooms
13.3 Exceptional (15)Located in Greenport, this apartment is by the sea. Sylvester Manor and Havens House are local landmarks, and some of the area's attractions include East End Seaport Maritime Museum and Railroad Museum ... -
Southold - United States
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
- 2 Guests 1Bedroom
12.8 Exceptional (168)Located in Greenport, this apartment is near the beach. 67 Steps Beach and Norman E. Klipp Marine Park reflect the area's natural beauty and area attractions include East End Seaport Maritime Museum and ... -
Southold - United States
Sea Breeze Paradise: Beachfront & Panoramic Views
- 6 Guests 3Bedrooms
12.5 Exceptional (48)Offering sea views, Sea Breeze Paradise: Beachfront & Panoramic Views is an accommodation set in Southold, 2.2 km from McCabe’s Beach and 36 km from Splish Splash. The accommodation offers a 24-hour front ... -
Southold - United States
Sensational, newly remodeled waterfront Greenport condo
- 4 Guests 2Bedrooms
10 Exceptional (5)Located in Greenport, this condo is on the waterfront. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced at Greenport Carousel and Kontokosta Winery. ... -
Southold - United States
Greenport Village Vacationer's Delight
- 7 Guests 3Bedrooms
12 Exceptional (6)Situated in Greenport, 41 km from Splish Splash, Greenport Village Vacationer's Delight features air-conditioned accommodation with a patio and free WiFi. This holiday home features a garden. ... -
Southold - United States
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
- 6 Guests 2Bedrooms
13.1 Exceptional (207)Located in Greenport, this condo is in a rural area and on the beach. Railroad Museum of Long Island and East End Seaport Maritime Museum are cultural highlights, and some of the area's attractions include ... -
Southold - United States
Spacious apartment, 3 blocks to downtown and steps to fishing pier.
- 4 Guests 2Bedrooms
10 Exceptional (62)Located in Greenport, this apartment is in the city center and near the beach. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced at Greenport Carousel ... -
Southold - United States
Private & Spacious Five Room Suite<br>Steps To Bay Beach and walk to Village.
- 4 Guests 2Bedrooms
10 Exceptional (145)Located near the beach, this apartment is in Pipes Cove, a neighborhood in Greenport. Sylvester Manor and Havens House are local landmarks, and some of the area's attractions include Railroad Museum of ... -
Southold - United States
First Floor 1905 Victorian home in the heart of Greenport Village
- 6 Guests 2Bedrooms
9.8 Exceptional (68)Located in Greenport, this apartment is near the beach. Sylvester Manor and Havens House are local landmarks, and the area's natural beauty can be seen at 67 Steps Beach and Norman E. Klipp Marine Park. ... -
Southold - United States
2 Bedroom Apartment in Historic Home with private yard (WBH)
- 4 Guests 2Bedrooms
9.4 Exceptional (35)Located in Southold, this apartment is in a rural area and near the beach. Croteaux Vineyards and Corey Creek Winery are worth checking out if an activity is on the agenda, while those looking for area ... -
Southold - United States
Beautiful Soundfront condominium
- 6 Guests 2Bedrooms
6 Pleasant (1)This condo is located in Greenport. Horton Point Park and Sylvester Manor are local landmarks, and the area's natural beauty can be seen at 67 Steps Beach and Norman E. Klipp Marine Park. Railroad Museum ... -
Southold - United States
4BR NOFO Home in Heart of Wine Country (w/ Pool)
- 8 Guests 4Bedrooms
Set in Southold, 4BR NOFO Home in Heart of Wine Country (w/ Pool) offers accommodation with private pool, free WiFi and free private parking for guests who drive. The air-conditioned accommodation is 3 ... -
Southold - United States
Steve's Place Well Furnished Heated Pool
- 6 Guests 3Bedrooms
13.3 Exceptional (12)Featuring air-conditioned accommodation with a private pool, Steve's Place Well Furnished Heated Pool is situated in Southold. It is set 35 km from Splish Splash and features a 24-hour front desk. ... -
Southold - United States
Goose Creek Getaway: Modern Home with Beach Access
- 5 Guests 3Bedrooms
13.3 Exceptional (3)Situated in Southold, within 35 km of Splish Splash, Goose Creek Getaway: Modern Home with Beach Access offers accommodation with air conditioning. The accommodation features a 24-hour front desk, an ATM ...
Bed and breakfast offers in Southold by the sea
Are you looking for an accommodation in Southold and do you want to save money? Choose from 12 Bed & Breakfasts in Southold
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Southold - United States
House on Chase Creek
- Hotel
11.6 Exceptional (235)Set in Shelter Island Heights, House on Chase Creek offers 4-star accommodation with a garden and a terrace. The property has sea and lake views. The bed and breakfast offers rooms with air conditioning, ... -
Southold - United States
Shorecrest Bed and Breakfast
- Hotel
11.7 Exceptional (83)Offering a private beach area, Shorecrest Bed and Breakfast is located in Greenport. Free WiFi access is available. Each room here will provide guests with a flat-screen cable TV and offer a garden or ... -
Southold - United States
West Neck Guesthouse
- Hotel
10.1 Exceptional (72)Situated in Shelter Island Heights, West Neck Guesthouse features free bikes and garden. This bed and breakfast features free private parking and a housekeeping service. The bed and breakfast has family ... -
Southold - United States
Sweet Dreams Bed and Breakfast Cutchogue
- 4 Guests 2Bedrooms
10 Exceptional (16)Situated in Cutchogue, 2.7 km from Fleet Neck Beach and 25 km from Splish Splash, Sweet Dreams Bed and Breakfast Cutchogue features accommodation with air conditioning and access to a garden. ... -
Southold - United States
Seven - a boutique B&B on Shelter Island
- Hotel
9.8 Exceptional (63)Just 450 metres to the beach, this bed and breakfast is located in Shelter Island Heights. A free breakfast is served each morning. Cable TVs are provided in each room at Seven - a boutique B&B on Shelter ... -
Southold - United States
The Stirling House Waterfront Inn Greenport
- Hotel
9.7 Exceptional (20)This Greenport bed and breakfast is located on the water and offers free Wi-Fi and individually decorated rooms equipped with electric fireplaces. Island’s End Golf & Country Club is 2 miles away. ... -
Southold - United States
A Walk in the Woods Bed and Breakfast
- Hotel
8.5 Fabulous (35)Relax on the large wrap-around front porch of this Long Island, New York bed and breakfast. Free Wi-Fi and daily breakfast are offered. Cedar Beach is 1 mile away. ... -
Southold - United States
The North Fork Loft
- 4 Guests 2Bedrooms
Located in Peconic, this guesthouse is on the waterfront. Mattebella Vineyards and Sannino's Bella Vita Vineyard are worth checking out if an activity is on the agenda, while those looking for area attractions ... -
Southold - United States
Vine & Sand--Southold NY's Newest B&B
- 8 Guests 4Bedrooms
33 km from Splish Splash, Vine & Sand--Southold NY's Newest B&B is a recently renovated property located in Southold and provides air-conditioned rooms with free WiFi and private parking. ... -
Southold - United States
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
- 2 Guests 1Bedroom
This bed & breakfast is located in Southold. Peconic Bay Winery and Railroad Museum of Long Island are local attractions and those in the mood for shopping can visit Greenport Farmers' Market and Harbes ... -
Southold - United States
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
- 2 Guests 1Bedroom
This bed & breakfast is located in Southold. Railroad Museum of Long Island and East End Seaport Maritime Museum are cultural highlights, and travelers looking to shop may want to visit Greenport Farmers' ... -
Southold - United States
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
- 2 Guests 1Bedroom
Located in Southold, this bed & breakfast is near the beach. Horton Point Park and Sylvester Manor are local landmarks, and some of the area's activities can be experienced at Corey Creek Winery and Croteaux ...
Farmhouse or Hotel? Choose from the best offers
Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?
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Farmstays in Southold -
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Hotels in Southold
Southold and the best offers per the best accommodation
What is the best period with the best offers to stay in Southold? If you are looking for accommodation in Southold during the best period without the chaos of mass tourism, the low season month with the best tariffs is in the month of January. The week with the best prices for that month is the week from 01-20 to 01-27.
If instead you are looking for accommodation in Southold during the high season, to enjoy the destination and it's capacities, the month of June is right for you. The most amount of accommodation available at the most convenient price is during the week that spans from from 06-22 to 06-29.
Southold is a touristic destination where the accommodation has an average cost of 599 Canadian dollars per night.
What to do in Southold
Southold: What's the weather like?
Southold: are you wondering about the weather you might find during your holiday? Befor organizing a holiday we always think about the wheather we might find when we get there. In Southold the average yearly temperature is 14°C. During the hottest month, which in this case is July, the temperature can get up to 25°C.
Instead the coldest month is January, reaching a minimum temperature of 2°C.
Instead the coldest month is January, reaching a minimum temperature of 2°C.
