Kent Island vacation rentals
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Top-rated vacation rentals in Kent Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Apartment in Stevensville
4.97 out of 5 average rating, 239 reviewsBoutique by the Bay
Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.
Aug 16 – 23
Home in Stevensville
4.94 out of 5 average rating, 185 reviews❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/3 acres of outdoor living! Perfect for Families & sleeps 14. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (14 max.). Book Today!
Feb 17 – 24
Apartment in Pasadena
4.99 out of 5 average rating, 542 reviewsSea Dreamer aka Phenomenal Hospitality
Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.
Nov 16 – 23
Vacation rentals for every style
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Popular amenities for Kent Island vacation rentals
Other great vacation rentals in Kent Island
Home in Shady Side
5.0 out of 5 average rating, 113 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Mar 18 – 25
Home in Annapolis
4.96 out of 5 average rating, 103 reviewsHistoric Downtown in-law suite
Jan 9 – 16
Bungalow in Deale
4.86 out of 5 average rating, 353 reviewsCozy waterfront getaway on the Bay
Jan 24 – 31
Cottage in Wittman
4.9 out of 5 average rating, 134 reviews"Wittman Cottage"
Dec 27 – Jan 3
Guesthouse in Annapolis
4.97 out of 5 average rating, 195 reviewsRECENTLY RENOVATED Cottage Near Downtown Annapolis
Oct 18 – 25
Home in Rock Hall
5.0 out of 5 average rating, 102 reviewsBayside Beach House
Jun 1 – 8
Guesthouse in Annapolis
4.99 out of 5 average rating, 102 reviewsCoastal Waterfront 1 Bedroom Cottage
Apr 29 – May 6
Cottage in Edgewater
4.99 out of 5 average rating, 123 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Nov 11 – 18
Cottage in Annapolis
4.96 out of 5 average rating, 328 reviewsRelaxing Water Views - Mill Creek Cottage
Dec 21 – 28
Apartment in Edgewater
4.92 out of 5 average rating, 396 reviewsPet Friendly Garden Apartment Near Annapolis
Aug 2 – 9
Guesthouse in Riva
4.99 out of 5 average rating, 273 reviewsThe Riva House
Mar 2 – 9
Apartment in North Beach
4.97 out of 5 average rating, 100 reviewsBayside Oasis of Southern Maryland
Nov 4 – 11
Other great vacation rentals in Kent Island
Cottage in Stevensville
4.93 out of 5 average rating, 15 reviewsCozy, Waterfront Getaway “The Great Nest”
Oct 9 – 16
Home in Stevensville
5.0 out of 5 average rating, 20 reviewsAway at the Bay: New Home on the Chesapeake Bay!
Mar 12 – 19
Home in Stevensville
4.95 out of 5 average rating, 40 reviews25-50% Off~Private Beach~Hot Tub~Fire Table~
Oct 5 – 12
Home in Stevensville
4.98 out of 5 average rating, 61 reviewsBeautiful Kent Island Getaway with Pool
Nov 12 – 19
Guesthouse in Chester
5.0 out of 5 average rating, 39 reviewsWaterfront Guest Cottage: Sunsets, Pool, Pier
Jan 11 – 18
Home in Stevensville
5.0 out of 5 average rating, 15 reviewsImpressive Waterfront Home - Pool, Pier, & Sunsets
Apr 8 – 15
Home in Stevensville
5.0 out of 5 average rating, 34 reviewsThe Pool House in Romancoke On The Bay
Oct 22 – 29
Home in Stevensville
5.0 out of 5 average rating, 99 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Aug 15 – 22
Home in Stevensville
5.0 out of 5 average rating, 28 reviewsBayview Bungalow - Water view, EV charging station
Sep 18 – 25
Home in Stevensville
4.97 out of 5 average rating, 95 reviewsThe Kent Island House
May 2 – 9
Barn in Queenstown
5.0 out of 5 average rating, 40 reviewsWaterfront Modern Guest Barn
Aug 23 – 30
Home in Stevensville
4.85 out of 5 average rating, 48 reviewsCheerful & Spacious Shore Life Beauty!
Nov 28 – Dec 5
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- Rentals with beach access Kent Island
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