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!

Oct 10 – 17

G$34,645 GYD per night

Guest favorite

Condo in Dennis

4.99 out of 5 average rating, 172 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Newly renovated, 250 sq ft studio at Near Beach Rentals. 300 yards to Glendon Beach means you can head to the beach in the morning and you're close enough to walk back for lunch. Fully furnished studio includes a queen bed and a fold down couch, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture. **(6) total units makes NBR a great place for larger gatherings!!!

Oct 12 – 19

G$26,185 GYD per night

Guest favorite

Condo in Chatham

4.96 out of 5 average rating, 279 reviews

In-town, Pied-a-Terre. Private, Sunny Comfy Home.

Bright, Sunny, fabulous in-town location. CLEAN, SAFE & PRIVATE hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, business trips, overflow guests. Comfortably furnished, thoughtfully outfitted. Quality linens, duvet etc. Walk to restaurants, cafe/bakery, groceries, shops, ballpark, Oyster Pond Beach, CBI, tennis courts, bike path, bike rental, etc etc. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

Jan 5 – 12

G$39,104 GYD per night

Guest favorite

Guest suite in Harwich

4.99 out of 5 average rating, 543 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.

Oct 24 – 31

G$35,579 GYD per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 116 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Oct 23 – 30

G$14,621 GYD 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

Sep 27 – Oct 4

G$45,520 GYD per night

Guest favorite

Guest suite in Brewster

4.95 out of 5 average rating, 150 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.

Sep 28 – Oct 5

G$21,143 GYD per night

Guest favorite

Apartment in Eastham

4.95 out of 5 average rating, 206 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 9 – 14

G$35,687 GYD 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.

Jan 14 – 21

G$27,312 GYD per night

Guest favorite

Guest suite in Orleans

4.92 out of 5 average rating, 143 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 16 – 23

G$28,760 GYD per night

Guest favorite

Cottage in Eastham

4.91 out of 5 average rating, 188 reviews

Classic Cape Cod Cottage

15 min walk to the best bayside beach. Very peaceful setting. Four night minimum stay from April 15 to June 15. June 15 to Sept 10 there's a 7 night minimum stay, from Saturday to Saturday. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore.

Apr 14 – 21

G$33,308 GYD per night

Guest favorite

Guest suite in Orleans

4.99 out of 5 average rating, 205 reviews

Private Beach, Cozy Cape Cottage

Enjoy your own private beach with soaring seabirds and ocean breeze! Let a breathtaking sunrise and view of the bay greet you every morning from bed. Take in the waterfront view on the outside patio by the garden or in the enclosed sun porch. Escape to our cozy cottage secluded in the woods with nearby trails. Explore the Cape's many attractions and refresh your soul with a relaxing Cape Cod vacation.

Mar 23 – 30

G$59,897 GYD per night