
Holiday rentals with a pool in Eastern Shore of Virginia
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Eastern Shore of Virginia
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!
Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

The Rosé Retreat: Kayaks-Screened Porch-RELAX
Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Blue Heron WaterSide
Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

Historic Rousby Hall, Waterfront, Pool, Beach
**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

3N+ Promo| Waterfront | Beach+Gamerm+Kayak+Firepit
*Ask about our 3+ Night promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

Wtrfrnt aptmnt w/pool/dock on private farm
Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

Heartsong Farmhouse , a nature lover's retreat.
Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

Magical wooded cottage pool +priv hottub walk2town
Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

3 BR Cottage on Mallardee Farm in Williamsburg
Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Peaceful Haven: nature, pool & charming town
Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.
Popular amenities for Eastern Shore of Virginia rentals with a pool
House rentals with a pool

THE OLD BEACON 1 | Beach Living

Wooded Wonderland Miniature Golf Hot tub Pool

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

York River Vacation Home

Paint The Beach Pink! Full House | Private Pool

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Country Comfort Close to the Beaches

Stunning waterfront panoramic view getaway house
Apartment rentals with a pool

Beautiful Beachfront Condo

Oceanfront Family Oasis: Pool, Beach & Parking!

Ocean & Bay Views - Local Family Owned & Operated

Oceanfront Gem VaB Studio Exceptional Views

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Ocean Pines Getaway

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Other holiday rentals with a pool

Private pool, waterfront, kayaks, bikes, firepits!

Sunrise Shore Waterfront; Private pool & hot tub!

Country Living Guest House (Upstairs/Downstairs)

Luxury Farmette -Private & Secluded-1hr to DC

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Pelican Place, Cozy Retreat | Pool | Walk to Tides

Big Cozy Loft Overlooking the Farm and River

Modern Lofty Tranquil 757
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Jersey Shore Holiday rentals
- Outer Banks Holiday rentals
- Ocean City Holiday rentals
- The Hamptons Holiday rentals
- South Jersey Holiday rentals
- Waterfront rentals Eastern Shore of Virginia
- Fitness-friendly rentals Eastern Shore of Virginia
- Cottage rentals Eastern Shore of Virginia
- House rentals Eastern Shore of Virginia
- Villa rentals Eastern Shore of Virginia
- Rentals with a hot tub Eastern Shore of Virginia
- Townhouse rentals Eastern Shore of Virginia
- Flat rentals Eastern Shore of Virginia
- Rentals with beach access Eastern Shore of Virginia
- Family-friendly rentals Eastern Shore of Virginia
- Rentals with a patio Eastern Shore of Virginia
- Rentals with a washing machine and dryer Eastern Shore of Virginia
- Apartment rentals Eastern Shore of Virginia
- Beachfront rentals Eastern Shore of Virginia
- Rentals with a fireplace Eastern Shore of Virginia
- Hotel rentals Eastern Shore of Virginia
- Bed and breakfasts Eastern Shore of Virginia
- Pet-friendly rentals Eastern Shore of Virginia
- Rentals with a firepit Eastern Shore of Virginia
- Rentals with an accessible-height toilet Eastern Shore of Virginia
- Rentals with a cinema Eastern Shore of Virginia
- Cabin rentals Eastern Shore of Virginia
- Rentals with an accessible-height bed Eastern Shore of Virginia
- Rentals with outdoor seating Eastern Shore of Virginia
- Rentals with breakfast Eastern Shore of Virginia
- Rentals with an EV charger Eastern Shore of Virginia
- Rentals with lake access Eastern Shore of Virginia
- Rentals with a kayak Eastern Shore of Virginia
- Rentals with pools Virginia
- Rentals with pools United States
- Chesapeake Bay
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Assateague Island National Seashore
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Assateague Beach
- Buckroe Beach and Park
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Wilkins Beach
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park
- Salt Ponds Public Beach
- Guard Shore
- Parramore Beach
- Gloucester Point Beach Par