Photo by Marie

Search Vacation Homes in Ridgely

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Vacation Homes in Ridgely

Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Property grounds

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

10.0 out of 10, Exceptional, (17)
"It was a awesome great comfy house."
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Luxury Treehouse with Large Deck
Interior

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (1)
"The treehouse was a perfect retreat to relax. Every detail of the property was well thought out and a relaxing spot to wind down from a long day. I loved waking up amongst the trees in the morning. The porch was perfect for coffee and loved the cows! We hope to be back soon. "
Luxury Treehouse with Large Deck
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Fridge, microwave, oven, stovetop

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

10.0 out of 10, Exceptional, (4)
"Thank you for a beautiful stay! Well appointed kitchen, comfortable beds and a pristine lot. "
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (9)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Dining

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (11)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Family & Friends Paradise – Pool, BBQ, & More!
Pool

Family & Friends Paradise – Pool, BBQ, & More!

10.0 out of 10, Exceptional, (1)
"This is such a great house and property! It's really close to St. Michael's without being right in town. Every bedroom has an ensuite bathroom which makes it great for multiple guests, the kitchen is well stocked, AC worked wonderfully, the pool is such a plus, etc. Thank you!"
Family & Friends Paradise – Pool, BBQ, & More!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor pool

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (131)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (15)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Sprawling Waterfront Home with views, Dock and In-Home Theatre
Outdoor dining

Sprawling Waterfront Home with views, Dock and In-Home Theatre

Sprawling Waterfront Home with views, Dock and In-Home Theatre
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (37)
"A must book!"
Serene Waterfront Cottage with dock and gorgeous views.
3 Mi to Dtwn: Townhome w/ Deck in Dover
Fridge, microwave, stovetop, dishwasher

3 Mi to Dtwn: Townhome w/ Deck in Dover

10.0 out of 10, Exceptional, (1)
"Absolutely beautiful home! Our stay was very comfortable and relaxing. The host was extremely gracious."
3 Mi to Dtwn: Townhome w/ Deck in Dover
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AED 724
AED 1,608 total
includes taxes & fees
30 Jun - 1 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Exterior

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

10.0 out of 10, Exceptional, (16)
"Return visitors loving Seventh Haven ❤️"
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Fridge, microwave, oven, stovetop

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (14)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (71)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
St. Michaels Escape – Walk to Town!
Fridge, microwave, oven, stovetop

St. Michaels Escape – Walk to Town!

St. Michaels Escape – Walk to Town!
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Marina

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (86)
"My family (9 of us ages 30-63) stayed at the sunset house for what have been our 30th family vacation. This house was perfect. Great location to St Michael’s, Easton and Oxford made for "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free