Vacation rentals in Little Pleasant Bay

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Top-rated vacation rentals in Little Pleasant Bay

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Guest favorite

Place to stay in Wellfleet

4.98 out of 5 average rating, 163 reviews

WoodsideTiny House near Wellfleet Bay

Our tiny house tucked under trees is the perfect getaway. Walk past our orchard to get to your "Romantic Hideaway". This special rental has a private, sunny deck, a Nordic shower, stained glass windows and a library of books/vinyls. Set back from a quiet road on our property, this little gem is walking distance to Wellfleet's center, harbor & many restaurants, & just minutes drive from National Seashore beaches & ponds. A fun time in bustling Provincetown awaits you only 15 miles down the road!

Sep 21 – 28

$148 per night

Guest favorite

Apartment in Harwich

4.9 out of 5 average rating, 263 reviews

The Secret Garden

Bright and spacious garden level apartment. One floor living, one queen bedroom, private bath, living room with queen pullout and limited kitchenette. Tranquil setting. Your own entrance and patio. A mile to Pleasant Bay, Eastward Ho golf course and Wequassett Inn, shopping, restaurants and beach. Your own private patio. Walk the labyrinth, gardens and fairy gardens. Take an outdoor shower. Cable TV in bedroom as well as living room plus wifi. The hosts live on the top floor of the home.

Mar 22 – 29

$125 per night

Guest favorite

Condo in Brewster

4.87 out of 5 average rating, 162 reviews

Shining Sea Condo

Ocean Edge condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. One king bed and one queen, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC in living room and heat throughout the unit. Wifi and two smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

Feb 26 – Mar 5

$89 per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 542 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

Feb 9 – 16

$149 per night

Guest favorite

Apartment in East Orleans

4.94 out of 5 average rating, 258 reviews

Cozy Waterfront Apartment, Private Beach Access

Hello to all of my future guests. I want to wish you all well and safety in these uncertain times. I can assure you that this property is safe, private, spotless and affords you access to a beautiful private beach. I have updated the apartment to include a microwave and two kayaks. We are implicating extra sanitizing and cleaning measures to ensure the apartment is clean and safe for each guest! Please stay safe, optimistic, and let me know of any concerns. Sincerely, Patty

Jan 7 – 14

$190 per night

Guest favorite

Apartment in Brewster

4.95 out of 5 average rating, 144 reviews

Sophisticated, Private Cape Cod living

LOCATION: 3/4 mile off main road (unpaved road). Located on the town line of Brewster and Orleans with less than 5 minutes to Chatham or Harwich by car. Nauset and Skaket beaches are less than 3 miles away. Nickerson state park less than 1 mile away. Cape Cod National seashore is located within 7.2 miles of our property. Shopping on Main Street in Chatham is 15 minutes. Enjoy a nice, tranquil walk, listen to the birds or feast your eyes on the surrounding conservation land.

Nov 19 – 26

$113 per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 149 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

Feb 2 – 9

$83 per night

Guest favorite

Apartment in Eastham

4.95 out of 5 average rating, 205 reviews

National Seashore Escape

There is no interaction required with hosts during stay. 1/4 mile to National Seashore Salt Pond Visitor Center and 2.0 miles to Coast Guard Beach, rated America's 6th best beach in 2019 by Dr Beach. The studio is above the garage with a private entrance private bath with shower. Queen bed, wifi, whisper quiet mini split a/c no window unit, tv. There is a kitchenette with refrigerator, microwave, coffee maker, toaster, sink, no stove.

Sep 2 – 7

$155 per night

Guest favorite

Guest suite in Harwich

4.94 out of 5 average rating, 226 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

May 4 – 11

$114 per night

Guest favorite

Condo in Dennis

4.84 out of 5 average rating, 164 reviews

The 5 minute walk to beach Super Cute Beach Condo

This conveniently located rental is just a 3 minute walk to the beach. This studio (245 sq ft) has 1 queen size bed, sleeper sofa, galley kitchen, dishes and silverware, pots and pans, refrigerator, microwave, coffee maker, WiFi, cable TV, beach chairs and umbrella and 2 boogie boards. There is a private patio with a table and a Webber Grill. PLEASE NOTE THE FOLLOWING: WE DO NOT PROVIDE LINENS OR TOWELS. THE BED IS QUEEN SIZE

Apr 23 – 30

$65 per night

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 142 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

Sep 24 – Oct 1

$120 per night

Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 342 reviews

Barn Cottage on Minister Pond

Newly renovated cozy heated Barn Cottage (not attached to house- privacy!) on Minister Pond with dock access to canoe/ new queen size bed/equipped kitchen/large deck overlooking pond/gas grill/private yard/2 minutes to ocean or bay beaches and bike trail in National Seashore/ many local attractions, and restaurants! Please note the new 12.45% short term rental tax is now in effect and will be added to your base. Thank you

Nov 21 – 28

$125 per night