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Holiday Rentals in Chesapeake

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    ₹ 10,222 Average
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    ₹ 0₹ 68,000+
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    Don't let other travellers get your favourite Chesapeake area holiday home. You're so close to securing your perfect getaway. Book today.
    All 26 Rentals in Chesapeake
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    Stay at the Quay!1 / 30
    (2)Excellent
    Chesapeake
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Chesapeake Bay 'BigBay' Beach House1 / 19
    (20)Excellent
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometres of Chesapeake.
    2 Bedroom |Family-Friendly Vacation Rental - Walk To Beach1 / 10
    (20)Very good
    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom1 / 51
    (1)Excellent
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This cottage is the perfect place to stay in Norfolk. We have enjoyed the deck by the water immensely as well as the sunroom, outdoor swing and hammock. The view is incredible...
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    About this property
    This cozy vacation home on 0.6 acres has a wonderful view of the Elizabeth river. It is a very special, unique, sweet and private place right on the cove. We offer: - A clean beautiful waterfront home - Complimentary breakfast/coffee while watching the sunrise over the dock - WiFi internet and...
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    Norfolk, Virginia 23502
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    'Beauty and the Beach'1 / 58
    (1)Excellent
    Norfolk
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Ocean Views
    • Waterfront
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegance, contemporary style, perfectly hand wrapped in seclusion. A luxurious masterpiece designed for those who live life on top. Delicately placed on the peaceful shores of the Chesapeake Bay, just a wind's whisper from Va Beach and the Ocean. Offering close to 4,000 sq. ft. and featuring 3...
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    Norfolk, Virginia 23503
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Beachfront Bluez    the Oceans Melody1 / 64
    (9)Very good
    Norfolk
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Wi-Fi
    • Waterfront
    • Grill
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2018
    Lots of room in this nice house. There were just a few of us, but a bigger group would be very comfortable. Quick access to the beach. The great view from the big deck is across...
    Reviewed 10 June 2018
    Beautiful, spacious home. It has a large porch, and that is where we spent most of our time! It rained most of our stay, so were very especially pleased to have the porch...
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    About this property
    Embrace 'Beachstreet Bluez', a carefully themed custom 3 level beachfront oasis. With hints of musical accents, reinforced by rhythmic views, while echoed by wonderful shades of charismatic blue(z). Imagine New Orleans' Bourbon Street, but on the beach. 'Jazz' up your travel plans by retreating at...
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    Norfolk, Virginia 23518
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    Norfolk
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Balcony
    • Central Heating
    • Terrace
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coastal Virginia at it's best! This beautiful, big beach house sits right on the dune and Chesapeake Bay! With 5 bedrooms (1 King, 5 queen, 4 baths, two dining room tables seating 12 plus bar seating, and fully equipped kitchen this is a perfect family get together! The porches, decks and...
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    Norfolk, Virginia 23503
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Norfolk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable three bedroom house is located in a quiet neighborhood. The house has a real homely feel to it. Newly renovated to put you in a mellow mood while relaxing in a fresh new look. All in all a great living area, with a fully equipped kitchen, two Queen sized beds, two singles (+one...
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    Norfolk, Virginia 23503
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Relaxing Chesapeake Bay Home for Rent1 / 36
    (1)Excellent
    Norfolk
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Secure Parking
    • Washer
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2018
    What a fabulous vacation for our three generations! The main living area was large enough for us to gather and spend time together. We ate nearly every meal on the porch...
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    About this property
    Come enjoy our beautiful five bedroom home within steps to the Chesapeake Bay. Huge master bedroom and expansive views of the bay. Opening living space, with three large out door decks. Please visit Vacation Rental By Owner to book. Property number 717981. Fish, Hunt for Shells, or just walk...
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    Location Information
    Norfolk, Virginia 23518
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Community
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Charming 3 bedroom 2 and 1/2 bathroom 1,672 sq. ft townhouse is equipped with everything you need to feel completely furnished with your comfort in mind. So if you decide to relax inside and enjoying a home cooked meal away from home. Guess what! We've got the bases covered. We provide a fully...
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    Location Information
    Community, Virginia 23453
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Caicos Cottage    a beach lovers dream1 / 80
    (3)Very good
    Norfolk
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Ocean Views
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2018
    Had a amazing time. Home was very clean, and I’m picky. Great views, easy beach access, we’ll really it’s not an access the house is literally on the sand. It’s just gorgeous...
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    About this property
    Similar to the islands of Turks & Caicos it is named after, this home may not be the largest in its region, but more than makes up for it with the awesomeness and uniqueness of its experience. This updated Cottage style respite, is nestled directly on the beach (literally), on a million...
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    Norfolk, Virginia 23518
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    *New Listing for 20171 / 20
    (1)Excellent
    Norfolk
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that the pictures show the house unfurnished. However updated pictures will be uploaded as soon as possible. Great home for the summer season. This home is fully furnished ready to receive you and your family! Great open floor plan for entertaining along with enough room for...
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    Location Information
    Norfolk, Virginia 23518
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Norfolk
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit this lovely bayside Norfolk vacation rental townhome, ideally settled within walking distance of the Chesapeake Bay. With 3 bedrooms, 3.5 bathrooms, 2,437 square feet, and accommodations for up to 8 guests, this is the perfect home for families of all sizes! You'll love the prime...
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    Location Information
    Norfolk, Virginia 23503
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your swimsuits and head off to the Chesapeake Bay by booking this 2-bedroom, 2-bathroom vacation rental apartment in Norfolk. Complete with all the comforts of home, this classic home offers 2 stories, 1,200 square feet of living space, and accommodations for up to 5 guests! With the beach...
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    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Apartment is 2 blocks from the beach. You’ll love it because of the new pillow-top comfy bed, the kitchen, and the condo is modern and cozy. It's a comfortable one bedroom end unit and the master sleeps two, but the futon pulls out to sleep another two. It's good for couples, solo adventurers,...
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    Norfolk, Virginia 23518
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Terrace
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exquisitely furnished 1bdrm New York loft style luxury condo with interior brick, and Brazilian hardwood floors throughout. Stainless steel island with industrial grade updraft and ventilation system. Granite counters throughout kitchen and master bath. Flat screen 3-D television with your favorite...
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    Norfolk, Virginia 23510
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Community
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Charming 3 bedroom 2 and 1/2 bathroom 1,672 sq. ft townhouse is equipped with everything you need to feel completely furnished with your comfort in mind. So if you decide to relax inside and enjoying a home cooked meal away from home. Guess what! We've got the bases covered. We provide a fully...
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    Community, Virginia 23453
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    *Waterfront**10 Mile View**Hot Tub**Pet Friendly**1 / 31
    (1)Excellent
    Norfolk
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2016
    Very nice house. On the water looking at a marina & across the river is a Naval yard with aircraft carriers, destroyers, and daily helicopters practicing. Even a seal...
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    About this property
    This house has waterfront views from every Room! Crabbing/fishing off large deck, (1 of 4 decks) Owned/managed by military veteran, (thanks for your support)! **Sail boat races on Thursday can be seen from the decks & giant ships! **BEACHES ** 50 steps behind home is a small community beach, 3...
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    Norfolk, Virginia 23503
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Community
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Charming 3 bedroom 2 and 1/2 bathroom 1,672 sq. ft townhouse is equipped with everything you need to feel completely furnished with your comfort in mind. So if you decide to relax inside and enjoying a home cooked meal away from home. Guess what! We've got the bases covered. We provide a fully...
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    Location Information
    Community, Virginia 23453
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Community
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Charming 3 bedroom 2 and 1/2 bathroom 1,672 sq. ft townhouse is equipped with everything you need to feel completely furnished with your comfort in mind. So if you decide to relax inside and enjoying a home cooked meal away from home. Guess what! We've got the bases covered. We provide a fully...
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    Location Information
    Community, Virginia 23453
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cozy Mother-in-Law Suite1 / 7
    (1)Excellent
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2016
    After my trip from Dallas it was nice to walk in to a place that felt just like home even for such a short stay. Very well kept, clean and fresh. I would definitely recommend...
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    About this property
    This carefree suite is fully furnished for a comfortable experience. We provide all bed and bath linens for your convenience. just bring your bags and the rest is waiting for you. Our suite offers a quiet beach environment... but for those wanting a night on the town....the Virgina Beach Boardwalk...
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    Location Information
    Norfolk, Virginia 23518
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come soak up the sun at this 2-bedroom, 1-bathroom Norfolk vacation rental apartment, ideally situated within close walking distance of Chesapeake Bay. With accommodations for 5 people, this beach getaway property boasts tasteful nautical decor, a view of the bay, and tons of nearby beachside...
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    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Community
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Virginia Beach Vacation Paradise. 3 bedroom, 2 bath home centrally located for access to town center, the beach, and local attractions. More information The space- Our home is warm and welcoming so make yourself at home and enjoy your stay. It's all yours! You'll only need to share the space with...
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    Community, Virginia 23453
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Waterfront
    • Hot Tub
    • Ocean Views
    • Balcony
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A picture is worth a thousand words so just look at the views of the sunrise from your master suite. Then crawl into your indoor hot tub and watch the dolphins jumping each morning and night. When the urge strikes you walk down to the beach and just take a deep breathe. If you are up for some...
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    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an affordable location 50 steps from the beach? This 2 bedroom, 1 bath apartment leads to a walkway with stairs to a white sandy beach on the Chesapeake Bay. The very affordable rental rate offsets not being able to see the beach from the apartment, but 50 steps cannot be beat for the...
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    Norfolk, Virginia 23503
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sail away in your dreams on this adorable Vintage sailboat! A truly unique experience, walking distance to the beach through the pristine East Beach neighborhood. Basic creature comforts in a gorgeous spot! Hang out with the local 'pirates' at the Lagoon and swap stories of adventures on the high...
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    Norfolk, Virginia 23518
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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