Vacation rentals with a pool in Dover

4.89 out of 5 average rating, 111 reviews

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Escape to Seasons on Mount Snow & stay in our fully equipped 2 bedroom (ski in/out) condo. Our location is the best on the mountain ... right between the main face & Carinthia Freestyle Park! Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities where you can relax in a hot tub, pool or sauna. See below for info on activities in the warmer months including hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

A cozy seating area features two woven chairs adorned with striped cushions. A small table holds a decorative vase with flowers, set against large windows that frame a vibrant backdrop of autumn foliage outside.

4.91 out of 5 average rating, 114 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

A warm gas fireplace is centrally positioned against a light-colored wall, complemented by a wood mantle and slate surround. A flat-screen TV is mounted above. A window allows natural light to brighten the area, while a desk and chair provide a workspace option.

4.97 out of 5 average rating, 181 reviews

Premier Stratton Village Location - Pool & Hot Tub

-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and grill, multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

5 out of 5 average rating, 98 reviews

A modern chalet is nestled among trees displaying autumn colors, featuring a welcoming front porch with two chairs. The entryway is highlighted by an arched window and natural greenery surrounds the home, enhancing its tranquil setting.

Cabin in Wilmington

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

4.99 out of 5 average rating, 256 reviews

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

4.9 out of 5 average rating, 156 reviews

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

4.91 out of 5 average rating, 151 reviews

A spacious living area features large windows that allow natural light to fill the room, highlighting a stone fireplace and wooden accents. A comfortable sofa is arranged near a coffee table, with a dining area visible in the background, creating a cozy gathering space.

Cabin in Wilmington

Chic Chalet | Hot Tub · Clubhouse · Mt. Snow

Escape to The Sugar Maple Chalet, your stylish family retreat in the heart of Wilmington, Vermont. This thoughtfully updated four-bedroom home blends cozy charm with modern comforts—think high-speed Wi-Fi, a private outdoor hot tub, and a fun-filled basement bar and game room. Just a few minutes from local shops, restaurants, ski slopes, and scenic hiking trails. One well-behaved pet is welcome to join the adventure! AC installed when temperatures average above 78 degrees.

4.95 out of 5 average rating, 180 reviews

A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.

Cabin in Guilford

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.

4.87 out of 5 average rating, 243 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

4.98 out of 5 average rating, 164 reviews

A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.

Barn in Newfane

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.

4.85 out of 5 average rating, 130 reviews

Walk to Mt. Snow-Spa-Summer Pool

*Amenity rich studio only a 5 minute walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

4.96 out of 5 average rating, 155 reviews

The living area features a spacious arrangement of comfortable brown couches, positioned around a wooden coffee table. A large, framed landscape photograph adorns the wall above, while natural light filters through large glass doors leading to a small outdoor deck.

Townhouse in Dover

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

Renovated 3-level, 2 bedroom+ twin sleep loft, 2.5 bathroom townhouse on Mt Snow. For the non-snowy months, enjoy the outdoor heated pool, gas fire pit, grill, tennis courts & hiking trails up the mountain as well as other great local activities, lakes and festivals near by. In the winter, take the shuttle 1 mile to the mountain and take the private ski trail back home. NOTE: Pool is Open between Memorial Day & Labor Day

Popular amenities for Dover rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 202 reviews

The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.

Home in Salem

Magical Farm Getaway - a must visit!

Superhost

A cape-style farmhouse is nestled beneath the expansive green canopy of a large tree. The house features multiple windows and a spacious deck, while the surrounding lawn is dotted with sunlight and shrubbery, creating a serene outdoor environment.

Home in Colrain

4.89 out of 5 average rating, 134 reviews

The 1770 House

5 out of 5 average rating, 23 reviews

Home in Wardsboro

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

4.88 out of 5 average rating, 180 reviews

A comfortable living area features a sectional gray sofa adorned with decorative pillows, a coffee table at the center, and two armchairs. Natural light filters in through large windows dressed in light curtains, illuminating the hardwood floor and creating a cozy atmosphere.

Home in Wilmington

Adams Farm-"The Little Farmhouse"

4.93 out of 5 average rating, 227 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

4.91 out of 5 average rating, 105 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

5 out of 5 average rating, 19 reviews

A charming house is nestled among greenery, featuring a screened-in porch with a red door. Low shrubs and flowering trees frame the entrance. Soft light filters through the trees, highlighting the natural surroundings and offering a sense of tranquility.

Home in Dummerston

Woodsy Retreat with Private Pool

The spacious living room features a large, sectional grey couch and a white armchair, arranged around a wooden coffee table. A brick wood-burning fireplace is situated against a wooden wall, with a mounted TV above it. The room is illuminated by warm lighting.

4.98 out of 5 average rating, 62 reviews

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

Condo rentals with a pool

A circular outdoor pool is surrounded by a landscaped area, featuring several trees and bushes. The building's large glass entrances reflect natural light. Sun loungers are positioned nearby, and a set of steps leads from the pool to the patio area.

4.97 out of 5 average rating, 67 reviews

Stratton Mt Summer: Golf, tennis, hike, bike, swim

Superhost

The exterior of the lodge features a blend of stone and wood elements, with multiple balconies and large windows reflecting the surrounding landscape. The entrance is framed by a welcoming staircase, leading to the main doorway marked with a sign that reads 'Hardwood Lodge'.

4.92 out of 5 average rating, 38 reviews

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

4.95 out of 5 average rating, 21 reviews

A spacious living area features a comfortable sectional sofa, positioned near large windows that provide natural light and a view of the outdoors. A cozy fireplace with a wood-burning option adds a touch of warmth, accompanied by a flat screen TV and a small table with chairs.

Condo in Ludlow

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

5 out of 5 average rating, 16 reviews

Luxury Condo * 3BD/3BA * Fall Foliage

4.93 out of 5 average rating, 114 reviews

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.

Condo in Proctorsville

One Bedroom Suite Near Okemo

A spacious living area features a large sectional sofa adorned with decorative pillows. Natural light floods in through sliding glass doors, offering views of an outdoor balcony. A stone fireplace adds warmth to the room, complemented by a wooden coffee table and tasteful artwork on the walls.

5 out of 5 average rating, 17 reviews

1st Fl Condo 3BR @ Stratton Sleeps 7 Pool, Hot Tub

4.93 out of 5 average rating, 14 reviews

A spacious living area features a wood-burning fireplace set against a textured stone wall. A large sectional sofa and additional seating surround a circular coffee table. Natural light enters through glass doors leading to a deck, complemented by green curtains that frame the view.

Condo in Ludlow

Elegant 3BR with Fireplace & Shuttle to Slopes

A scenic view of lush green hills is presented from a balcony. The landscape is dotted with trees and fields, while a gravel path leads into the distance. Two blue adirondack chairs add a cozy touch to the outdoor space.

4.91 out of 5 average rating, 22 reviews

Mountainside Condo- 3bed/3Bath with amazing views.

Other vacation rentals with a pool

A blue wooden chalet is surrounded by greenery, featuring large glass windows that provide views of the interior. A small outdoor deck leads to a hot tub, positioned against the backdrop of vibrant autumn foliage.

4.9 out of 5 average rating, 20 reviews

Private chalet | hot tub, shuttle & ski home trail

4.94 out of 5 average rating, 87 reviews

The living room is furnished with a blue sofa and a light armchair, complemented by wooden side tables and lamps. A coffee table is positioned centrally on a carpeted floor. Walls are adorned with wood paneling and artwork, enhancing the space's rustic charm.

Townhouse in Dover

Cozy Bear- 1 mile to Mt Snow Ski Home

A cozy living area features a sectional gray sofa with decorative pillows and a matching armchair. Natural light filters through large windows, illuminating a wooden coffee table with drinks. A wall-mounted television is visible above a stone fireplace, with a patterned area rug beneath.

4.9 out of 5 average rating, 10 reviews

Lodge on the Loop: pet-friendly, hot tub & sauna

4.92 out of 5 average rating, 13 reviews

An indoor hot tub is featured, with bubbling waters capturing natural light from nearby windows. A seating area with lounge chairs is positioned next to the hot tub, providing a relaxing environment within the clubhouse. The walls are accented with wooden panels, enhancing the space's warmth.

Townhouse in Dover

Mount Snow Best View - Sauna|HotTub|Pool|Fireplace

A private hot tub is situated on a spacious deck, surrounded by trees and illuminated by soft outdoor lighting. The backdrop features a well-designed chalet with large windows, allowing a glimpse into the inviting interior space.

5 out of 5 average rating, 22 reviews

Bears Den Chalet | Hot Tub, Community Pool & More!

A cozy living area features a large brown sectional sofa and a circular coffee table, placed on a patterned rug. Natural light enters through a window covered with sheer curtains. A television is mounted on the wall, and decorative accents complement the rustic wooden walls.

4.92 out of 5 average rating, 13 reviews

Townhouse at Mount Snow

5 out of 5 average rating, 7 reviews

A stone fireplace, framed by a metal screen, showcases a flickering fire. The surrounding area features a blend of light-colored stones, and a wooden mantle rests above. A decorative item sits nearby, contributing to a warm and inviting atmosphere.

Cabin in New Ashford

Rustic Cabin with Wood Fireplace