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42 Houses

17

Deerpond Carriage House

Maryland / Woolford

Woolford guest house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Price per night from

$179

Price per night from

$179

Great rentals within 20 miles that match your search

Distance approx 9.48 km from Woolford

42

Waterfront Room Rentals 2 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$100

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$100

Distance approx 9.48 km from Woolford

(1) Very Good 

34

Waterfront Room Rentals 1 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$130

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$130

Distance approx 7.67 km from Woolford Show on Map

16

Choptank River View House

Maryland / Cambridge

Cambridge house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

Price per night from

$1,000

Price per night from

$1,000

Distance approx 7.42 km from Woolford Show on Map

29

NEW! Colonial Home in Cambridge w/Wraparound Porch

Maryland / Cambridge

Cambridge house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$221

Responds fast!
avg. 9 minutes

Price per night from

$221

Distance approx 13.6 km from Woolford

(4) Excellent 

20

Best kept secret by the bay (Entire House)

Maryland / Fishing Creek

Fishing Creek house

3 4 3 nights min

  • 3 bedrooms
  • sleeps 4
  • 3 nights min
  • Air conditioning
  • Private garden

Price per night from

$168

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$168

Distance approx 9.49 km from Woolford

(5) Average 

55

Waterfront Vacation Home with Private Beach

Talbot County / Trappe

Trappe house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 97 mi
  • Child Friendly

Price per night from

$329

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$329

Distance approx 9.48 km from Woolford

44

Waterfront Room Rentals 3 with Private Beach

Talbot County / Trappe

Trappe room

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$100

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$100

Distance approx 19.42 km from Woolford

24

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Calvert County / Chesapeake Beach

Chesapeake Beach apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$70

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$70

Distance approx 18.57 km from Woolford

4

St. Michaels Area Waterfront Retreat with pier, pool, kayaks and bikes

Talbot County / Royal Oak

Royal Oak house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$595

Price per night from

$595

Distance approx 15.84 km from Woolford

(1) Excellent 

18

St. Michaels Waterfront Home W/Dock for 2 boats

Talbot County / Neavitt

Neavitt house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$224

Price per night from

$224

Distance approx 15.6 km from Woolford

10

Harbor Cottage at the Chesapeake Bay

Calvert County / St. Leonard

Saint Leonard cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$260

Price per night from

$260

Distance approx 13.04 km from Woolford

(2) Very Good 

33

Chesapeake Bay Waterfront on Hoopers Island with Private Beach

Maryland / Fishing Creek

Fishing Creek house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$295

Price per night from

$295

Distance approx 19.21 km from Woolford

(24) Excellent 

27

Location Location! St Michaels-- In Town Cottage!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary
“Crabtastic Great Escape” This cottage is the perfect great escape. Conveniently located in the middle of quaint St Michael's close to the harbor, restaurants, and shops. The property is clean and well-maintained with beautiful landscaping. The buildin
…see more

Price per night from

$150

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$150

Distance approx 16.22 km from Woolford

(6) Excellent 

20

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

Talbot County / Tilghman

Tilghman cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t
…see more

Price per night from

$199

Price per night from

$199

Distance approx 15.76 km from Woolford

28

St. Michaels Area Cottage - Walk to Water & Marina

Talbot County / Neavitt

Neavitt house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$175

Responds fast!
avg. 9 minutes

Price per night from

$175

Distance approx 17.11 km from Woolford

18

Historic Waterfront Property with Wi-Fi and Dock

Talbot County / St. Michaels

St. Michaels house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$746

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$746

Distance approx 19.18 km from Woolford

(11) Very Good 

30

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

Talbot County / St. Michaels

St. Michaels house

7 9 min stay varies

  • 7 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that
…see more

Price per night from

$289

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$289

Distance approx 6.59 km from Woolford Show on Map

8

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Maryland / Cambridge

Cambridge house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$869

Price per night from

$869

Distance approx 16.14 km from Woolford

8

Cottage 1a at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

Price per night from

$244

Price per night from

$244

Distance approx 19.19 km from Woolford

(13) Excellent 

24

Premier Cottage in St. Michaels- In Town Location!

Talbot County / St. Michaels

St. Michaels house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$150

Responds fast!
avg. 3 hours 32 minutes

Price per night from

$150

Distance approx 15.98 km from Woolford

10

Business or Leisure?

Calvert County / Lusby

Lusby guest house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$65

Responds fast!
avg. 3 hours 37 minutes

Price per night from

$65

Distance approx 18.93 km from Woolford

(3) Excellent 

24

Best sunrise in St. Michaels....Broadview Bay House

Talbot County / St. Michaels

St. Michaels house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$597

Price per night from

$597

Distance approx 16.34 km from Woolford

(1) Excellent 

9

Cottage 2 at Grandview Pleasure Point

Talbot County / Bozman

Bozman house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$386

Price per night from

$386

Distance approx 17.98 km from Woolford

15

Tranquil Easton Waterfront Property

Talbot County / Easton

Easton house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$597

Price per night from

$597

Distance approx 2.22 km from Woolford Show on Map

(12) Very Good 

31

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Maryland / Cambridge

Cambridge house

6 20 min stay varies

  • 6 bedrooms
  • sleeps 20
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle
…see more

Price per night from

$497

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$497

Distance approx 16.14 km from Woolford

6

Cottage 1b at Grandview Pleasure Point

Talbot County / Bozman

Bozman cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$244

Price per night from

$244

Distance approx 13.37 km from Woolford

(4) Excellent 

38

Hoopers Island Studio, 360 Degrees WATER VIEWS

Maryland / Fishing Creek

Fishing Creek apartment

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 32 mi
  • Ask about children
“What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and
…see more

Price per night from

$155

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$155

Distance approx 13.68 km from Woolford

9

Eastern Shore Waterfront Home, Ready for Spring and Summer!

Maryland / Fishing Creek

Fishing Creek house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$224

Price per night from

$224

Distance approx 16.54 km from Woolford

(5) Excellent 

22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

Talbot County / St. Michaels

St. Michaels house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$373

Price per night from

$373

Distance approx 19.35 km from Woolford

14

Halo's Haven Guest Quarters

Talbot County / St. Michaels

St. Michaels house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$325

Price per night from

$325

Distance approx 18.69 km from Woolford

12

Harris Cove Cottages LLC

Talbot County / St. Michaels

St. Michaels cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$199

Price per night from

$199

Distance approx 16.34 km from Woolford

(13) Excellent 

34

Main House at Grandview at Pleasure Point

Talbot County / Bozman

Bozman house

5 13 7 nights min

  • 5 bedrooms
  • sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite.
…see more

Price per night from

$686

Price per night from

$686

Distance approx 17.13 km from Woolford

24

NEW! Historic Hoopersville Home on Chesapeake Bay!

Maryland / Fishing Creek

Fishing Creek house

7 17 min stay varies

  • 7 bedrooms
  • sleeps 17
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$295

Responds fast!
avg. 9 minutes

Price per night from

$295

Distance approx 18.97 km from Woolford

7

St. Michael's Premier in Town Summer Cottage!

Talbot County / St. Michaels

St. Michaels house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$284

Price per night from

$284

Distance approx 16.46 km from Woolford

(10) Excellent 

24

RESTORED WATERFRONT COTTAGE

Talbot County / Royal Oak

Royal Oak cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$299

Price per night from

$299

Distance approx 2.67 km from Woolford Show on Map

(15) Excellent 

35

Year Round Estate on Bay / Fam. Reunions / Slps 28

Maryland / Cambridge

Cambridge house

7 28 min stay varies

  • 7 bedrooms
  • sleeps 28
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop
…see more

Price per night from

$1,000

Price per night from

$1,000

Distance approx 4.97 km from Woolford Show on Map

(10) Excellent 

50

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Maryland / Cambridge

Cambridge cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$167

Price per night from

$167