Sailwinds Park, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Sailwinds Park, Maryland on RentalSaver.com!

Sailwinds Park Rentals

From $435 per night (USD)
VRBO
Beautiful Colonial Home on the Choptank River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to this newly updated 4-bedroom, 2-bath colonial home for a fun-filled retreat on the Cambridge coast! Offering k ...
From $435 per night (USD)
VRBO
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Expedia
Historic 1918 House 1/2 Block from the Choptank River
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This old fisherman's home in the historic district of Cambridge has been recently renovated and is close to restaurants, ...
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Expedia
From $288 per night (USD)
VRBO
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Conductor's Rest, a fully renovated 2-bedroom historic condo nestled in the heart of downtown Cambridge, Mary ...
From $288 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Cambridge is waiting for you at this enchanting 4-bedroom house. Step inside and be greeted by the amazing decor that ex ...
From $223 per night (USD)
Expedia
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $277 per night (USD)
VRBO
The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to The Drinking Gourd...a freshly renovated 2-bedroom penthouse in the heart of the historic downtown district o ...
From $277 per night (USD)
VRBO
From $1007 per night (USD)
Expedia
Gorgeous retreat across from yacht club, the Choptank, and IronMan finish line!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The perfect location for an easy getaway in any season. The home is across the street from the IRONMAN Maryland finish l ...
From $1007 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Sailwinds Loft at Cambridge Creek
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterview second story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located j ...
From $174 per night (USD)
VRBO
$Aurora Blue - A Stylish Experience \n$
From $270 per night (USD)
VRBO
Aurora Blue - A Stylish Experience \n
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $270 per night (USD)
VRBO
From $284 per night (USD)
VRBO
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy historic Cambridge all year at this fully stocked and freshly renovated 2 bedroom, 2.5 bath townhouse across the s ...
From $284 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $545 per night (USD)
VRBO
From $866 per night (USD)
VRBO
House close to Great Marsh Park and Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance t ...
From $866 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Spacious, pet-friendly 3-bedroom home
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape to this updated, single-level home with 3 bedrooms, a separate office (with doors), high-speed wifi, a large FENC ...
From $339 per night (USD)
VRBO
From $557 per night (USD)
VRBO
The Water's Edge Rental Cambridge, Md - sleeps 10, 4 bedrooms
Bedrooms:
0
Bathrooms:
4
Sleeps:
10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $557 per night (USD)
VRBO
From $537 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is fully visi ...
From $537 per night (USD)
VRBO
From $375 per night (USD)
VRBO
High Water Guest House<br>
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of h ...
From $375 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Stylish Victorian in Historic District
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beware: not your typical VRBO A hunt has been set for you and your companions to follow the dramatized story of Eva Rob ...
From $407 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Waterviews, Comfort & Convenience!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking for some rest or relief…or perhaps just a little fun? This home is just steps away from the Cambridge Yacht Basi ...
From $383 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Walk to Park & River: Dog-Friendly Cambridge Gem
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing Area Whether you’re here to explore Cambridge ...
From $180 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Walkable Condo w/ Drawbridge Views in Cambridge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Community Pool | Walk to Happy Hour at Portside | River-View Balcony Dive into waterfront serenity at this Cambridge va ...
From $216 per night (USD)
VRBO
From $127 per night (USD)
Expedia
Station House East: Upscale Loft in the Historic District Cambridge, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Step into style and comfort in this beautifully appointed 1-bedroom, 1.5-bath condo located in the iconic Four Corners ...
From $127 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Cambridge Apt in Walkable Neighborhood
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $160 per night (USD)
VRBO
From $351 per night (USD)
VRBO
Walk to Dtwn: Waterfront Eastern Shore Townhome!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $351 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Casual Bungalow close to Choptank River, sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A newly renovated pristine bungalow close to downtown Cambridge, MD. We are conveniently located near St. Michael, East ...
From $254 per night (USD)
VRBO
From $295 per night (USD)
Expedia
New, Intown Waterfront Townhome wPool & Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Perfect, large property for an extended, family or group stay at this superb Chesapeake retreat -- part of a ga ...
From $295 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Family-Friendly Cambridge Home w/ Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape the hustle and bustle of your busy lives and retreat to this 3-bedroom, 2.5-bathroom vacation rental home! Along ...
From $390 per night (USD)
VRBO
From $320 per night (USD)
Expedia
New listing! Riverside Retreat on the Choptank River
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview renta ...
From $320 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Magnificent Historic Home by Water is Ready!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Our house, built in 1736, is ideally located in the heart of historic Cambridge. Facing the Choptank River, it is 1/2 bl ...
From $610 per night (USD)
VRBO
From $191 per night (USD)
VRBO
Modern Cambridge Cottage: Walk to Town, Waterfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Pairing modern comforts with timeless charm, this 1-bath studio offers an ideal stay on your next visit to coastal Cambr ...
From $191 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Luxury on the river, steps to downtown &boat ramp!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautifully crafted 1915 Sailmakers home nestled perfectly off the choptank harbor. Newly renovated with stunning appoin ...
From $366 per night (USD)
VRBO
From $298 per night (USD)
Expedia
A Kozy Waterfront Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
About this space From the balcony of this Kozy Waterfront Condo, enjoy relaxing sunsets overlooking the marina, and a bi ...
From $298 per night (USD)
Expedia
From $683 per night (USD)
VRBO
Choptank River Beach Home w/ Pier in Cambridge!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Riverfront Location | In-Unit Washer & Dryer | Gas Grill for Group Cookouts Your next waterfront retreat awaits at thi ...
From $683 per night (USD)
VRBO
From $393 per night (USD)
VRBO
1915 Historic Cambridge Property w/ Fire Pit!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Experience the deep-rooted history of Cambridge when you book this 5-bedroom, 3.5-bathroom vacation rental. This ideally ...
From $393 per night (USD)
VRBO
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VRBO
The Yellow Victorian in Historic Cambridge – Walk to Everything!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The best kept little secret! Historic Cambridge, less than 2hours from DC/VA and 1 hour to the beach. House is located j ...
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VRBO
$Charming 4 bedroom in Historic Cambridge\n\n$
From $527 per night (USD)
VRBO
Charming 4 bedroom in Historic Cambridge\n\n
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Enjoy the old world charm of this home, built in 1894 in the historic district of the picturesque and diverse town of Ca ...
From $527 per night (USD)
VRBO
From $219 per night (USD)
VRBO
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this fully renovated historic condo nestled in the heart of downtown Cambridge, Maryland, with its fabulous d ...
From $219 per night (USD)
VRBO
From $374 per night (USD)
VRBO
< 1 Mi to Dtwn: Waterfront Townhome in Cambridge!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Private Deck w/ Views | 1,800 Sq Ft | Gated Community Your tranquil escape awaits at this modern and airy vacation rent ...
From $374 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Cheerful three-bedroom Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Introducing River Light Cottage, the perfect escape in historic Cambridge, Maryland! A short walk from downtown shops an ...
From $256 per night (USD)
VRBO

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Sailwinds Park Rentals

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Results: 37 Rentals