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Holiday rentals with beach access in Pioneer Valley

Find and book unique rentals with beach access on Airbnb

Top-rated rentals with beach access in Pioneer Valley

Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

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Cottage in Shutesbury

4.93 out of 5 average rating, 197 reviews

Lake Wyola House Shutesbury Massachusetts

Bright, airy recently remodeled three Bedroom lakefront home on Lake Wyola. Most rooms have a Lake View. Beds and bedding are new, each bed room has a ceiling fan. A super place to make awesome memories. Perfect for a family vacation or romantic getaway. (6 people, two cars max) Close to local colleges, Amherst, Northampton and many attractions. Comfortable and relaxing. Big Screen TVs in the livingroom and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

10–17 Apr

$463 SGD per night

Guest favourite

Guest suite in Granby

4.9 out of 5 average rating, 121 reviews

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

4–11 Feb

$145 SGD per night

Guest favourite

Flat in Woodstock Valley

4.93 out of 5 average rating, 337 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

UCONN Graduations coming soon, celebrate, relax. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. Featuring Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy private deck, propane fire pit, gaze at the moon & stars. Cook-Propane grill. Enjoy scenic walks around the lakes. Wake up to amazing sunrises. Pretty flowers, trees surrounding!! Now open-Woodstock Valley Country Store

16–23 Dec

$212 SGD per night

Guest favourite

Home in Vernon

4.99 out of 5 average rating, 115 reviews

Luxe Bolton Lake!

Now booking for summer! Relax and savor the tranquil vistas of picturesque Middle Bolton Lake while enjoying stylish comfort in our 2000+ sq. ft. 3 bedroom/3 bathroom architecturally-designed home. Amenities include expansive waterfront, outdoor jacuzzi, gorgeous master bedroom suite w/ private en suite bath, boutique toiletries, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, wifi, large deck, fire pit, kayaks, vintage canoe and much more. Come make lasting memories.

21–28 Jan

$683 SGD per night

Guest favourite

Cottage in Orange

4.94 out of 5 average rating, 132 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

15–22 Dec

$162 SGD per night

Guest favourite

Cottage in Becket

4.95 out of 5 average rating, 131 reviews

Cozy lakeside cottage

Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.

24 Nov – 1 Dec

$452 SGD per night

Guest favourite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

26 Jan – 2 Feb

$255 SGD per night

Guest favourite

Cabin in Petersburg

4.91 out of 5 average rating, 187 reviews

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

29 May – 5 Jun

$201 SGD per night

Guest favourite

Cottage in Orange

4.95 out of 5 average rating, 198 reviews

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a newly designed vacation home with breathtaking views of Tully Mountain. This 4-season Cottage has real salvaged barn wood walls; up-cycled maple floors and one-of-a kind scratch built furniture and lighting fixtures. The deconstructed architecture leaves exposed the electrical conduit and copper plumbing pipes, making the cottage feel alive and organic.

31 Jan – 7 Feb

$164 SGD per night

Guest favourite

Flat in Newfane

4.97 out of 5 average rating, 406 reviews

Rock River Retreat: Pets Welcome

You are welcome here with fresh air & room to run - your pet, too, when registered as an extra person! Your private guest suite awaits in a 1790's colonial on the Rock River in the quiet village of South Newfane, VT. Note: Recent floods in Vermont have thankfully not affected our home or guest experience. ❤️ PLEASE READ THE ENTIRE DESCRIPTION BELOW re: kitchenette & pet details.

27 Oct – 3 Nov

$188 SGD per night

Guest favourite

Cottage in Sturbridge

4.93 out of 5 average rating, 122 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Our petite (648 sq. ft.) lakeside cottage is the perfect place to unwind, relax and explore. Enjoy the spectacular unobstructed views of the sunset from the spacious deck (750 sq. ft.) from the comfort of your easy chair. The location of our cottage provides the tranquility of the lake, close to major routes and you will be minutes away from all that Sturbridge has to offer.

5–12 Jun

$339 SGD per night

Guest favourite

Guest suite in Charlton

4.86 out of 5 average rating, 381 reviews

Baker Pond Hideaway

Out in the country, on a lovely pond, we are in the woods with our own private beach. The rustic in-law apartment is on the ground floor of our house - bedroom (with small kitchenette) and bath, and a private entrance. Great for walks and canoeing and fishing and biking. We are only 65 miles from Boston, 15 minutes to Sturbridge Village.

13–20 Dec

$162 SGD per night

Holiday rentals for every style

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Popular amenities for rentals with beach access in Pioneer Valley

Free parking on premises

Air conditioning

Apartment rentals with beach access

Guest favourite

Flat in Wilmington

4.88 out of 5 average rating, 279 reviews

Globetrotter Retreat - Minutes to the Mountain

18–25 Oct

$151 SGD per night

Guest favourite

Flat in Newfane

4.85 out of 5 average rating, 124 reviews

Apartment at Five Ferns

8–15 Jun

$110 SGD per night

Flat in New Lebanon

4.95 out of 5 average rating, 128 reviews

Sunny Duplex at the old boarding house

14–21 Feb

$185 SGD per night

Guest favourite

Flat in Conway

5.0 out of 5 average rating, 42 reviews

House Above the Hollow

11–18 Oct

$190 SGD per night

Guest favourite

Flat in Canaan

5.0 out of 5 average rating, 88 reviews

Mountain View Getaway

13–20 Feb

$146 SGD per night

Guest favourite

Flat in Brattleboro

4.99 out of 5 average rating, 75 reviews

River View apartment 30 minutes to Mt Snow.

3–10 Aug

$184 SGD per night

Guest favourite

Flat in Otis

4.97 out of 5 average rating, 61 reviews

Enjoy every season the Berkshires have to offer.

27 May – 3 Jun

$232 SGD per night

Guest favourite

Flat in Coventry

5.0 out of 5 average rating, 51 reviews

Hide Away at Rock Farm UConn Private BnB “5 Star”

6–13 Jan

$181 SGD per night

House rentals with beach access

Guest favourite

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

12–19 Sep

$773 SGD per night

Guest favourite

Home in Coventry

5.0 out of 5 average rating, 105 reviews

Waterfront 10 min to Uconn outdoor tv gas fire pit

30 Nov – 7 Dec

$301 SGD per night

Guest favourite

Home in Sturbridge

4.96 out of 5 average rating, 174 reviews

Modern Lakeview House -Chef's Kitchen, Strong Wifi

23–30 Sep

$283 SGD per night

Guest favourite

Home in Coventry

4.94 out of 5 average rating, 162 reviews

Cozy Cottage * Coventry Lake* 15 min to UConn *

7–14 Apr

$222 SGD per night

Guest favourite

Home in Becket

4.87 out of 5 average rating, 289 reviews

Real Estate:Therapy - Lake, Laundry, Love it

21–28 Jul

$358 SGD per night

Guest favourite

Home in Monterey

4.93 out of 5 average rating, 116 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

17–24 Jun

$254 SGD per night

Guest favourite

Home in Newfane

4.97 out of 5 average rating, 115 reviews

Peaceful cabin close to skiing & Brattleboro

12–19 Apr

$417 SGD per night

Guest favourite

Home in Sharon

4.93 out of 5 average rating, 138 reviews

New Availability! Charming Farmhouse Group Getaway

20–27 Feb

$291 SGD per night

Destinations to explore