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Welcome to Pretty Picky Properties

We specialize in vacation rentals only, and only premier homes and cottages on the Lower Cape, mostly on or very near the beach. Please click on any of the photos below to see more photos of each of these Pretty Picky Properties. Then click on the "Contact" link at the left to reach us with any questions. We're eager to help you experience the Cape Cod summer vacation of your life!

NOTE: Rates and availability subject to owner confirmation.

Sleeps up to 12

Sleeps up to 10

Sleeps up to 8

Sleeps up to 6

Check Property Availabilities!

Property ID: 083-B

BREWSTER

Rare beach front home with plenty of living space

 

Please ask about June & September rates

Sleeps: 12

Bedrooms: 4

Baths: 2 full baths plus shower/dressing room

Wireless Internet

Property ID: 076-B

BREWSTER

Vacation togetherness & privacy in one big

Bayside home

 

In-Season: $5,800

Off-Season: Please ask

Sleeps: 12

Bedrooms: 6

Baths: 4 full plus outdoor shower

Central air conditioning

Wireless Internet

 

 

 

 

 

 

 

 

Property ID: 270-B

BREWSTER

Living space to spare in big family home by beach

 

In-Season: $5,200

Off-Season: Please ask.

Sleeps:12

Central air conditioning

Property ID: 061-B

BREWSTER

Superb new custom built home by the Bay

 

In-season: $6,200

Off-season: Please ask

Sleeps: 10

Bedrooms: 4 plus queen convertible

Baths: 3 full plus outdoor shower

Central air conditioning

Property ID: 055-E

EASTHAM

Spacious Eastham house, three-minute

walk to perfect, private beach

 

In-season: $5,300

Off-season: Pease ask

Sleeps: 10

Bedrooms: 5

Baths: 3 full plus outdoor shower

 

Property ID: 040-B

BREWSTER

Captivating property on Brewster beach

offers main cottage plus separate "4th

of July" house.

 

In-season: $5,500

Off-season: $4,500

Sleeps 10-11

Bedrooms: 6

Baths: 2 1/2 baths plus outdoor shower

Property ID: 590-O

ORLEANS

Exquisite Orleans summer home across the road from Pleasant Bay

beach

 

In-season: $4,800

Off-Season: Please ask.

Sleeps: 10

Air conditioning, wireless Internet

Property ID: 014-B

BREWSTER

Spacious new custom built home by the beach

 

In-season: $4,800

Off-season: Please ask

Sleeps: 10

Bedrooms: 4 plus extra room

Baths: 3 1/2

Central a.c., wireless Internet

Property ID: 037-O

EAST ORLEANS

Beachfront cottage, sweeping views of Nauset Beach

 

In-season: $5,000

Off-season: Please ask

Sleeps: 10

Bedrooms: 5

Baths: 2 full baths plus outdoor shower

Cable TV, high-speed Internet

Property ID: 012-B

BREWSTER

Sweeping Beach & Bay Views, Upscale Amenities Right on the Beach!

 

In-season: $6,500

Off-season: Please ask

Sleeps: 10

Bedrooms: 5

Baths: 2 plus outdoor shower

Washer/dryer, spare fridge,

multiple flat screen TVs, wi-fi

Property ID: 059-B

BREWSTER

Spacious, Comfortable Home Directly on

Sandy Beach

 

In-season: $6,500

Off-season: Please ask

Sleeps: 8-10

Bedrooms: 4

Baths: 3 1/2 plus outdoor shower

Property ID: 045-B

BREWSTER

Striking New Custom Built Home on the Beach

 

In-season: $6,500

Off-season: Please ask

Sleeps: 8-10

Bedrooms: 4

Baths: 3 1/2 plus outdoor shower

 

 

 

 

 

 

Property ID: 633-O

NORTH CHATHAM

Classic Renovated Sea Captain's Home Provides

the Perfect North Chatham Escape

 

In-season: $2,700

Off-season: Please ask

Sleeps 8-10

Bedrooms: 4

Baths: 2 1/2

Property ID: 047-B

BREWSTER

Roomy, bright vacation home sleeps 10, 4 minutes walk to beach.

 

In-season: $4,500

Off-season: Please ask

Sleeps 8-10

Bedrooms: 4

Baths: Three full, outdoor shower, hot tub

Wireless Internet, a.c. window units

Property ID: 046-O

EAST ORLEANS

5BR restored, tony Nauset Heights cottage overlooks the Atlantic.

 

In-season: $6,200

Off-season: $4,300

Sleeps 10-11

Bedrooms: 5

Baths: 2 1/2 plus outdoor shower

Central a.c., wireless Internet

Property ID: 059-WB

WEST BARNSTABLE

Stunning architect-owned home with pool and sweeping views

of SandyNeck

 

In-season: $3,200 - $3,500

Off-season: Please ask

Sleeps: 10

Bedrooms: 4

Bathrooms: 3 full

In-ground pool

Central air conditioning

Property ID: 045-E

EASTHAM

Large, premier quality Eastham home on private beach

 

In-season: $7,500

Off-season: Please ask

Sleeps 8-10

Bedrooms: 4

Baths: 3 full, 1 half bath

Property ID: 018-B

BREWSTER

Bayside gem with limited weeks,

unlimited quality.

 

In-season: $5000-$7,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 Baths: 3 1/2

Property ID: 067-B

BREWSTER

Directly on the beach, with sweeping

Bay views from virtually everywindow!

 

In-season: $5,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Property ID: 117-B

BREWSTER

The beachfront vacation you've always

imagined.

 

In-season: $4900

Off-season: Please ask

Sleeps: 8

Bedrooms: 5

Baths: 2 full plus outdoor shower

Property ID: 015-B

BREWSTER

Immaculate beach house just steps from

Cape Cod Bay

 

In-season: $4,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Wireless Internet, washer & dryer

Property ID: 090-B

BREWSTER

Sweeping Bay views from two-story cottage

directly on the beach.

 

In-season: $3,800

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 Baths: 1

Stackable washer/dryer

Property ID: 115-B

BREWSTER

Charm and privacy right on the beach

 

In-season: $4,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 1 full bath plus outdoor shower

Property ID: 222-B

BREWSTER

Pristine family cottage commands Bay

view

 

In-season: $4,400

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Property ID: 008-O

EAST ORLEANS

Idyllic vacation home just over the dunes from

secluded section of Nauset Beach.

 

In-season: $3,500

Off-season: $2,200

Sleeps: 8

Bedrooms: 4

Baths: 2 full plus outdoor shower

Property ID: 068-B

BREWSTER

Roomy cottage directly on Cape Cod

Bay. Air conditioning.

 

In-Season: $3,500

Off-Season: Please ask

Sleeps: 8

Bedrooms: 4, air conditioning

Baths: 1 full plus outdoor shower

Property ID: 260-E

EASTHAM

Cheery Vacation Home, Under 4-Minute Walk To Stunning Eastham Beach

 

In-season: $4,400

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 1/2 plus outdoor shower

Property ID: 019-D

DENNIS

European style spacious home in North Dennis

 

In-season: $2,500

Off-season: Please ask

Sleeps: 6-8

Bedrooms: 3

Baths: 3 full

Property ID: 105-B

BREWSTER

Light, bright vacation home on the Bay,

architect owned and renovated

 

In-season: $5,200

Off-season: Please ask

Sleeps: 8

Bedrooms: 3

Baths: 1 1/2 plus outdoor shower

Property ID: 030-O

EAST ORLEANS

Classic family summer beach house,

breathtaking views of Nauset Beach

and the Atlantic Ocean

 

In-season: $4,500

Off-season: Please ask

Sleeps: 8

Bedrooms: 6

Baths: 2 full plus outdoor shower

Property ID: 280-B

BREWSTER

Immaculate beach front house overlooking Cape Cod Bay

 

In-season: $5,200

Off-season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 2 1/2 plus outdoor shower

Property ID: 116-B

BREWSTER

Family vacation home directly on Cape Cod Bay

offers stunning view and very private yard

 

In-Season: $5,500

Off-Season: Please ask

Sleeps: 8

Bedrooms: 4

Baths: 3 full plus outdoor shower

Wireless Internet

Window air conditioners

Property ID 101-B

BREWSTER

Pond view and access, walk to Bay beach

 

In-season: $4,200

Off-season: Please ask

Sleeps 8

Bedrooms: 3

Baths: 3 full plus outdoor shower

Central air conditioning

Wireless Internet

Property ID 375-C

CHATHAM

Large, pristine Chatham home, private

tennis court. Walk to beach, Town.

 

In-season: $8,000

Off-season: Please ask

Sleeps: 8

Bedrooms: 5

Baths: 4 full

Air conditioning

Wireless Internet

Property ID 049-O

EAST ORLEANS

First time rental. As close as you can

get to Nauset Beach.

 

In-sseason: $5,000

Off-season: Please ask

Sleeps: 8-9

Bedrooms: 4

Baths: 2 full plus outdoor shower

Central air conditioning

Cable TV, wireless Internet

Property ID 013-O

ORLEANS

Pristine, secluded custom built home

includes heated pool.

 

In-season: $4,200

Off-season: Please ask

Sleeps 8

Bedrooms: 3

Baths: 3 1/2 plus outdoor shower

Central air conditioning

Cable TV, wireless Internet

Elevator from garage to main level

Property ID: 071-B

BREWSTER

Impeccably kept vacation beach house,

200 feet from the beach

 

In-season: $4,500

Monthly Rates: July & August $16,500-$17,500 (3-9% discount)

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 plus Family Room convertible

Baths: 2 full, 1 half bath, outdoor shower

Property ID: 036-C

NORTH CHATHAM

Newly updated, secluded home in North Chatham

 

In-season: $2,500

Off-season: Please dask

Sleeps: 8-10

Bedrooms: 3

Bathrooms: 3 full plus outdoor enclosed shower

Central air conditioning

Property 015-E

EASTHAM

Pristine Eastham Bayside Home with Separate In-Law Apartment

 

In-season: $2500-3000

Off-season: Please ask

Sleeps: 8

Bedrooms: 3 plus In-Law Apartment

Baths: 3 full, outdoor shower

Property ID 043-O

ORLEANS

Casual cottage elegance, directly

on Nauset Beach

 

In-season: $4,800

Off-season: $3,200

Sleeps: 6-8

Bedrooms: 2

Baths: 3 full plus two outdoor showers

Central air conditioning (new cottage)

Cable TV, wireless Internet

Property ID: 259-B

BREWSTER

Just renovated beach house on Cape Cod Bay

 

In-season: $4,500

Off-season: Please ask

Sleeps: 6-8

Bedrooms: 3

Baths: 1 full plus outdoor shower

Cable TV, wireless Internet

Property ID: 078-B

BREWSTER

Classic Cape Beach Cottage on Cape Cod Bay

 

In-Season: $3,600

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full plus outdoor shower

Property ID: 074-B

BREWSTER

Cozy cottage on private Bayside beach

 

In-Season: $3,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full plus outdoor shower

Property ID: 089-B

BREWSTER

Spacious beach house nestled in dunes,

100 feet to private sandy beach

 

In-season: $3,500

Off-season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 1/2 plus outdoor shower

Property ID: 006-E

EASTHAM

Charming vacation hideaway, right on

the water

 

In-Season: $2,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 2

Full baths: 1

Property ID: 054-D

EAST DENNIS

Commanding Bay views & 100+ yards to sandy Dennis beach

 

In-season: $3,000

Off-sdeason: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 1 full, 1 half bath

Property ID: 077-C

CHATHAM

Spectacular water views and steps from

Main Street, Chatham

 

In-Season: $4,500

Off-Season: Please ask

Sleeps 6

4 Bedrooms

1 Full Bath, 2 half baths, plus outdoor shower

Property ID 260-B

BREWSTER

House on Beach with Extras

 

In-Season: $4,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 2 full plus outdoor shower

Window a.c units

Property ID: 588-O

ORLEANS

Beautifully renovated home, across the

road from sandy Pleasant Bay beach.

 

In-Season: $3,800

Off-Season: Please ask

Sleeps 6-8

3 Bedrooms

2 1/2 baths plus outdoor shower

Property ID: 326-C

CHATHAM

Impeccable Chatham vacation home

on Morris Island Road

 

In-Season: $5,200

Off-Season: Please ask

3 Bedrooms

3 Full baths, half bath plus outdoor shower

Sleeps 6

Property ID: 125-B

BREWSTER

Large, exquisite cottage, 300 feet from

perfect sandy beach on the Bay

 

In-Season: $4,200

Off-Season: Please ask

Sleeps: 6

Bedrooms: 4

Baths: 2 1/2 plus outdoor shower

Property ID: 063-B

BREWSTER

Spotless Brewster beach house wth Bay views

 

In-Season: $4,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 3 full baths

Property 012-C

CHATHAM

Comfy Colonial in quiet Chatham

neighborhood

 

In-Season: $2,500

Off-Season: Please ask

Sleeps: 6

Bedrooms: 3

Baths: 2 1/2

 

 

Property ID: 051-O

ORLEANS

 

Spectacular water views of Nauset Beach from classic Cape cottage

 

In-season: $4,900

Off-season: Please ask

Sleeps: 6-7

Bedrooms: 3

Baths: 3 Full Baths, plus outdoor shower

Property ID: 029-O

EAST ORLEANS

 

Spectacular views and 2 minute walk to Nauset Beach from this spacious beachside home.

 

In-season: $4950-$5200
Off-season: $ 3700
Sleeps: 8-10
Bedrooms: 5
Bathrooms: 3 full, 1 half, plus outdoor shower