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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May
Charming Cottage - Ultimate Relaxation Destination
Exterior

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (114)
"This was our second stay. It’s extremely convenient to Commonwealth Senior Living where my mother lives. This was a sweet little cottage to relax and regroup after some very hard days of moving her to Assisted Living. "
Charming Cottage - Ultimate Relaxation Destination
Virginia Retreat w/ Porch & Grill, Near Beaches!
Interior

Virginia Retreat w/ Porch & Grill, Near Beaches!

3.0 star property
Virginia Retreat w/ Porch & Grill, Near Beaches!
*SANDY HILL SUNSETS*
On the beach, sun-loungers

*SANDY HILL SUNSETS*

10.0 out of 10, Exceptional, (71)
"From start to finish, Christie was warm, friendly and welcoming. The hospitality and communication were off the charts. The private beach view is one of the most amazing views we experienced. Very private and a long stretch of beach to walk along. The place was clean and has everything you need from a basics standpoint. The surroundings were awesome. Lots of fields and nature to explore nearby with the golf cart. Highly recommend and will be back."
*SANDY HILL SUNSETS*
Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!
Property grounds

Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!

Beach Bettie's - Serene, charming cottage located on the Chesapeake Bay!
ESVA Down by the Sea & Pet Friendly
Exterior

ESVA Down by the Sea & Pet Friendly

9.4 out of 10, Exceptional, (3)
"My work team stayed here while on a project for Eastern Shore. It is a good location for our project. GPS did led us to the wrong location, but the homeowner helped. The house was clean, and the beds were comfortable. "
ESVA Down by the Sea & Pet Friendly
Unique Tangier Cottage w/ Chesapeake Bay Views!
Fridge, microwave, oven, stovetop

Unique Tangier Cottage w/ Chesapeake Bay Views!

10.0 out of 10, Exceptional, (5)
"My family has rented 10's of properties in the US and Europe over the past 20 years, and Bella Vista is in the top 3. If you are interested in a deeper exploration of this fascinating island, we highly recommend you stay here. The home was recently beautiful renovated and decorated, with pretty much every need met for in home meal preparation. I guarantee you will not need much else! We also highly recommend meal service offered, which will complete this amazing experience for you! P.S. the host...
Unique Tangier Cottage w/ Chesapeake Bay Views!
Smith Beach Beachfront Rental, Bay View Cottage, near Cape Charles, Virginia
Property grounds

Smith Beach Beachfront Rental, Bay View Cottage, near Cape Charles, Virginia

10.0 out of 10, Exceptional, (50)
"Totally enjoyed our stay. Very relaxing, very comfortable!"
Smith Beach Beachfront Rental, Bay View Cottage, near Cape Charles, Virginia
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
Outdoor dining

Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

9.4 out of 10, Exceptional, (19)
"Well equipped, quality kayak and sup options. Gorgeous views, sunsets. Intend to go back."
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
Relax and Renew on your private deck overlooking the Chesapeake Bay
Terrace/patio

Relax and Renew on your private deck overlooking the Chesapeake Bay

9.8 out of 10, Exceptional, (25)
"We had such a wonderful and relaxing week here! We loved the private waterfront deck - from our morning coffee to evening sunsets (which were stunning!) we spent most of our time there. The cottage was inviting and clean with nice beach decor and a very well-equipped kitchen and the cottage had just about anything you could need. Donna was a very responsive and accommodating host who met us and showed us around. She’s great! The only negatives we would have - and this is only because we are a...
Relax and Renew on your private deck overlooking the Chesapeake Bay
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Property grounds

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (5)
"Very nice property, we made good use of the dock and were able to launch my 18.5 ft boat from the concrete ramp. Fishing, crabbing, boating were good (though crabs a bit on small side) the cottage was clean, well organized and neat. Everything was really nice and Genevieve was extremely responsive and pleasant to deal with."
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
'Cora's Cottage' Near Chesapeake Bay Access!
Beach

'Cora's Cottage' Near Chesapeake Bay Access!

10.0 out of 10, Exceptional, (2)
"House was very clean and comfortable. Great spot for a family with young adults. Nice bike ride or walk to the beautiful water area. "
'Cora's Cottage' Near Chesapeake Bay Access!
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Private kitchen

Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks

3.0 star property
Stunning Chesapeake Bay Farmhouse w/ Dock & Kayaks
Charming Cape Charles Vacation Rental Home!
Private kitchen

Charming Cape Charles Vacation Rental Home!

3.0 star property
Charming Cape Charles Vacation Rental Home!
Charming Painter Home w/ Chesapeake Bay Views
Outdoor dining

Charming Painter Home w/ Chesapeake Bay Views

3.0 star property
8.0 out of 10, Very good, (1)
Charming Painter Home w/ Chesapeake Bay Views
The Waverly Tree House
Property grounds

The Waverly Tree House

The Waverly Tree House
Bungalow w/ Large Yard: 8 Mi to Cape Charles Beach
Exterior detail

Bungalow w/ Large Yard: 8 Mi to Cape Charles Beach

Bungalow w/ Large Yard: 8 Mi to Cape Charles Beach
The only place to be at sunset !!!
Beach nearby, sun-loungers

The only place to be at sunset !!!

The only place to be at sunset !!!
Unique Tangier Cottage w/ Chesapeake Bay Views!
Interior

Unique Tangier Cottage w/ Chesapeake Bay Views!

3.0 star property
Unique Tangier Cottage w/ Chesapeake Bay Views!
Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!
Interior

Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!

3.0 star property
Home w/ Fire Pit < 1 Mi to Willis Wharf Boat Ramp!
Waterfront cottage on Occohannock Creek w/ beautiful Chesapeake Bay sunset views
Beach nearby

Waterfront cottage on Occohannock Creek w/ beautiful Chesapeake Bay sunset views

10.0 out of 10, Exceptional, (6)
"It was as if I’d died and gone to heaven!!!! Thanks guys. I love you and your family so much. Thank you for extending your home to us."
Waterfront cottage on Occohannock Creek w/ beautiful Chesapeake Bay sunset views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Painter

Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Beach

Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay

10.0 out of 10, Exceptional, (1)
"This is a wonderful property if you are looking for a nice relaxing vacation. We thoroughly enjoyed our trip."
Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay
Nassawadox Creek Waterfront Home with Private Pool
Outdoor pool

Nassawadox Creek Waterfront Home with Private Pool

10.0 out of 10, Exceptional, (39)
"This is a beautiful house and Nancy is an outstanding host. We enjoyed sitting by the pool and birdwatching. My wife wanted to take the scenic main room home with us. "
Nassawadox Creek Waterfront Home with Private Pool
Charming Cottage - Ultimate Relaxation Destination
Exterior

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (114)
"This was our second stay. It’s extremely convenient to Commonwealth Senior Living where my mother lives. This was a sweet little cottage to relax and regroup after some very hard days of moving her to Assisted Living. "
Charming Cottage - Ultimate Relaxation Destination
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your cottage in Painter with Expedia?
Expedia has some superb cottages in Painter, so start planning for an unforgettable holiday on nature’s doorstep. If you’re on a budget, click on how much you want to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We’ll help you find the perfect digs whatever your style of travel or plans.
How can I find cheap cottages in Painter?
The simplest way to get cheap cottages in Painter is with Expedia’s filter tool. Fine-tune your search results by star rating, budget and amenities to discover excellent rates in a few clicks.
What is there to do in Painter near my cottage?
If you’d like to discover the sights of Painter, be sure to stop by The Blue Crow Antique Mall. It’s a hit among locals and visitors alike.