Holiday rentals in Oyster Pond

4.99 out of 5 average rating, 240 reviews

Guest suite in Chatham

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

5 out of 5 average rating, 9 reviews

Home in Chatham

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

4.97 out of 5 average rating, 374 reviews

Guest suite in Brewster

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

Place to stay in Wellfleet

4.97 out of 5 average rating, 239 reviews

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

4.99 out of 5 average rating, 120 reviews

Guest suite in Chatham

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

4.99 out of 5 average rating, 605 reviews

Guest suite in Harwich

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten 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.

4.97 out of 5 average rating, 264 reviews

Flat in Chatham

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

5 out of 5 average rating, 48 reviews

Holiday home in Chatham

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

4.95 out of 5 average rating, 59 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

Newly renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! Complete renovation of Windmill in 2022. This unique rental has one bedroom with king bed on second floor, with small full kitchen/dining area, two sitting/TV areas and full bathroom on first floor. Private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door! Perfect spot for your vacation!

4.96 out of 5 average rating, 332 reviews

Apartment in Chatham

In-town, Pied-a-Terre. Private, Sunny Urban Oasis

Bright, Sunny, great in-town location. CLEAN, SAFE & PRIVATE and spacious, hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Full Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

4.92 out of 5 average rating, 184 reviews

Guest suite in Orleans

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.

4.97 out of 5 average rating, 39 reviews

Home in Barnstable

1 minute walk to beach, Saturday to Saturday

The cottage duplex is across the street from Covell's Beach, we also have a private beach without life guard supervision. There is a family residing on the other side of the duplex. We offer an outdoor shower, grill, outdoor picnic area with an ocean view.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Oyster Pond holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oyster Pond

Apartment in Chatham

4.79 out of 5 average rating, 82 reviews

Lavish 1BR | Balcony | Washer/Dryer

Christopher CharlesRating, 5 stars6 days ago

Loved it, beautiful accommodations

5 out of 5 average rating, 6 reviews

Flat in Chatham

Chatham Studio- .5 mile to beach

CarsonRating, 5 stars5 days ago

This was a fantastic place to stay for the week on Cape Cod. Great host, great location, quiet place to stay with plenty to do 10 minutes away from the town, 2 minutes away from a great beach. The place was very clean and had everything we needed for a phenomenal trip.

4.95 out of 5 average rating, 76 reviews

Chatham Rose Arbors Artist Cottage

KimRating, 5 stars8 months ago

My husband and I came to Chatham for a long weekend to celebrate our wedding anniversary. This cottage is perfect for a couple and was very clean. A charming space with enough room for two, a stocked kitchenette, a comfy bed, and a spacious place for your bikes and outdoor things. Danielle and Brett provided two bikes, but we brought our e-bikes which were incredible for cruising around. We thoroughly enjoyed traveling along the amazing rail trails, which were super close by. Each morning we enjoyed the delicious coffee that was provided from Snowy Owl (loved grinding our own beans-the aromas were incredible) and also the fantastic local recommendations given to us by our hosts. They have a guitar which my husband played, making us feel right at home. We highly recommend this adorable clean bright space for a romantic getaway in lovely Cape Cod. It was close to everything and we loved being so close to “home” after dinners out in Chatham. 10 out of 10!!

Flat in Orleans

4.57 out of 5 average rating, 166 reviews

Modern Cape Apartment in Orleans, Private Entrance

JatnielRating, 5 stars6 days ago

My family and I had a great time at Michael’s. Everything was perfect!!

4.93 out of 5 average rating, 113 reviews

Chatham Cottage - Quiet and Quaint - Beach-Bicycle

ChristineRating, 5 stars8 months ago

Katie’s place was our first Airbnb experience and wow,superhost she is!!! She made us feel like old friends coming to visit. Made sure we had anything we needed even gloves on a chilly morning for our walk. Her place is a great location. Cottage is very warm and inviting. Katie gave lots of suggestions of places to see and go to. Would back for sure!

4.97 out of 5 average rating, 257 reviews

Cozy Cottage

RyanRating, 5 stars2 weeks ago

Had the best time in the cottage and around Chatham. Appreciated all the old-world charm of the place. Cynthia and Hutch were incredibly welcoming hosts and we hope to return soon.

4.96 out of 5 average rating, 179 reviews

Hotel room in Chatham

Main Suite - Chatham Guest Rooms

PatriciaRating, 5 stars3 weeks ago

What a fabulous stay in Bob’s beautiful apartment! This was my second visit, and I wouldn’t stay anywhere else. The spacious apartment is immaculately clean and very well appointed - Bob has thought of everything, and it is full of lovely touches. Very comfortable bed, cozy living room with a great library, well-equipped modern kitchen, a full-sized washer and dryer, and a wonderful bathroom with lots of storage. Bob is a very responsive host, and this charming accommodation gets my very highest recommendation!!