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79 Houses

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

(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

$385

Price per night from

$385

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

(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

$688

Price per night from

$688

Great rentals within 20 miles that match your search

Distance approx 16.96 km from Bozman

(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 16.4 km from Bozman

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

$996

Price per night from

$996

Distance approx 16.96 km from Bozman

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 14.93 km from Bozman

(5) Very Good 

17

Seahorse Guest Cottage near the Bay, dog friendly

Calvert County / North Beach

North Beach cottage

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$160

Responds fast!
avg. 12 minutes

Price per night from

$160

Distance approx 14.43 km from Bozman

26

Annapolis Crows Nest Cottage: Chesapeake Bay View

Maryland / Annapolis

Annapolis villa

5 20 min stay varies

  • 5 bedrooms
  • sleeps 20
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$693

Price per night from

$693

Distance approx 17.18 km from Bozman

26

Love Point Luxury Waterfront in Stevensville

Kent Island / Stevensville

Stevensville house

3 10 3 nights min

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

Price per night from

$1,394

Price per night from

$1,394

Distance approx 7.57 km from Bozman

(1) Excellent 

26

Huge Stevensville House Overlooking Eastern Shore!

Kent Island / Stevensville

Stevensville house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$399

Responds fast!
avg. 55 minutes

Price per night from

$399

Distance approx 4.94 km from Bozman

(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

$200

Price per night from

$200

Distance approx 2.84 km from Bozman

(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 14.81 km from Bozman

11

Panoramic Views of Herrington Harbour on the Bay.

Calvert County / North Beach

North Beach house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$498

Price per night from

$498

Distance approx 12.85 km from Bozman

24

Shady Side House on Chesapeake Bay Near Marina!

Maryland / Shady Side

Shady Side house

2 5 min stay varies

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

Price per night from

$185

Responds fast!
avg. 55 minutes

Price per night from

$185

Distance approx 18.27 km from Bozman

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

$866

Price per night from

$866

Distance approx 12.71 km from Bozman

(3) Excellent 

21

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Kent Island / Chester

Chester house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 14 mi
  • Child Friendly
“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,
…see more

Price per night from

$284

Price per night from

$284

Distance approx 4.82 km from Bozman

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

$747

Responds fast!
avg. 3 hours 21 minutes

Price per night from

$747

Distance approx 2.82 km from Bozman

(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 2.82 km from Bozman

(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 18.51 km from Bozman

(14) Excellent 

19

Love Point Waterfront

Maryland / Kent Island

Kent Island house

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Child Friendly
“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans
…see more

Price per night from

$249

Price per night from

$249

Distance approx 17.12 km from Bozman

11

Love Point Bay Vacation Home

Kent Island / Stevensville

Stevensville apartment

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$328

Price per night from

$328

Distance approx 16.63 km from Bozman

(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 18.04 km from Bozman

(2) Excellent 

52

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Maryland / Annapolis

Annapolis house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 mi
  • Child Friendly
  • Car not necessary

Price per night from

$249

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$249

Distance approx 19.21 km from Bozman

4

Perfect Annapolis with Lots of Parking & Hot Tub

Maryland / Annapolis

Annapolis townhouse

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$493

Price per night from

$493

Distance approx 2.94 km from Bozman

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 13.77 km from Bozman

12

Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

Kent Island / Chester

Chester house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$299

Price per night from

$299

Distance approx 16.53 km from Bozman

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

$180

Price per night from

$180

Distance approx 18.61 km from Bozman

(3) Very Good 

30

Beautiful Murray Hill Home (Annapolis)

Maryland / Annapolis

Annapolis house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decor
…see more

Price per night from

$424

Price per night from

$424

Distance approx 19.14 km from Bozman

4

Lochhaven house for rent

Maryland / Edgewater

Edgewater house

3 2 7 nights min

  • 3 bedrooms
  • sleeps 2
  • 7 nights min
  • Air conditioning
  • Private garden

Price per night from

$100

Price per night from

$100

Distance approx 3.27 km from Bozman

(1) Average 

38

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

Talbot County / St. Michaels

St. Michaels villa

6 12 2 nights min

  • 6 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool

Price per night from

$847

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$847

Distance approx 15.49 km from Bozman

43

The Yellow House- Gorgeous Southern Colonial

Maryland / Annapolis

Annapolis house

6 14 4 nights min

  • 6 bedrooms
  • sleeps 14
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$991

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$991

Distance approx 15.05 km from Bozman

(2)  

26

3BR Annapolis Home on Oyster Creek w/Amazing Views

Maryland / Annapolis

Annapolis house

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$349

Responds fast!
avg. 8 minutes

Price per night from

$349

Distance approx 14.19 km from Bozman

(15) Excellent 

35

Luxury vacation condominum with private beach

Kent Island / Chester

Chester house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Child Friendly

Price per night from

$439

Price per night from

$439

Distance approx 10.91 km from Bozman

(5) Excellent 

17

KI Golf House-A PAR for the Course & Mile to Beach

Maryland / Kent Island

Kent Island house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$598

Price per night from

$598

Distance approx 18.91 km from Bozman

(4) Excellent 

31

Charming Home close to historic district

Maryland / Annapolis

Annapolis house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$249

Responds fast!
avg. 59 minutes

Price per night from

$249

Distance approx 15.9 km from Bozman

(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

$996

Price per night from

$996

Distance approx 13.93 km from Bozman

(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

$168

Price per night from

$168