Holiday rentals with a pool in Somerset County

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Top-rated rentals with a pool in Somerset County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Condo in Carrabassett Valley
4.87 out of 5 average rating, 15 reviews

Great Location For All Your Outdoor Adventures!

This charming ski in/ski out condo is perfect for a family of four seeking to enjoy all that Sugarloaf has to offer. Make this your ideal home base for your vacation, conveniently located just a short walk across the lot to the mid-station chairlift, where your skiing adventure begins.The condo is clean and well-maintained, featuring one bedroom, a pull down queen size murphy bed, living room with gas fireplace, full bathroom and fully equipped kitchen. Laundry facilities on site & free parking!

Top Guest favourite
A two-story building is featured, with a spacious balcony providing seating options. Large windows on the upper level allow ample natural light. The ground floor has two garage doors, and the exterior is finished in white siding, set against a backdrop of trees.
Guest suite in Pittsfield
4.97 out of 5 average rating, 36 reviews

Angel Mist Retreat Garage Apartment

Looking to get away from the hustle and bustle. You have found it! Watch for wildlife, while sipping coffee from the balcony of this cozy and stylish walkup apartment located in central Maine just minutes from I-95 between Augusta and Bangor. Ideal location for professionals, couples and parents traveling into Maine who enjoy solitude, but appreciate the comforts of modern amenities. Includes two king beds, stocked kitchen, large dining table, wifi, balcony off livingroom and master bedroom.

Top Guest favourite
A cozy living area features a comfortable sofa and chairs arranged around a wooden coffee table. Two decorative wooden skis and vintage snowshoes adorn the wall. Natural light floods the space through large windows, overlooking the greenery outside. The room is completed with a ceiling fan and wall clock.
Condo in Carrabassett Valley
5 out of 5 average rating, 35 reviews

Slope Side Sugarloaf Condo

This classic slope side Sugarloaf condo, in Snowbrook Village is ideal for access to a wide range of outdoor activities. A short walk to Snubber Chairlift gets you up the mountain. The Carrabassett Valley Mountain Trail Network offer activities including Nordic skiing, snowshoeing, mountain & fat tire biking, and hiking on an extensive trail network, accessible year-round from our parking lot. New for 2025 lift access for summer mountain biking starting in July. TFSS four days of biking joy!

Guest favourite
The exterior of a three-story colonial home is showcased, featuring a large circular pool surrounded by a white fence. Lush green lawn and trees provide a serene backdrop, while a spacious deck extends from the house, offering ample seating and relaxation space.
Home in Newport
4.92 out of 5 average rating, 61 reviews

Maine Lakehouse Retreat with pool

Waterfront property on lake Sebasticook with 3 floors of living. Updated Colonial home with gourmet kitchen, granite countertops with island and farmhouse table overlooking a large deck with new 27' pool and a large lawn for family fun including a basketball court and 150' of waterfront with floating dock, canoe, Adult & youth kayaks & paddleboard. Short walk to boat landing, swimfront,riverwalk,restaurants, grocery stores, gas stations and more. Pontoon boat rental upon request pre-arrival.

Guest favourite
Apartment in Carrabassett Valley
5 out of 5 average rating, 11 reviews

Ski In Ski Out, Prime Location, Park & Walk!

Your family will enjoy unparalleled convenience when you stay at this centrally located condo on Sugarloaf Mountain. This prime location offers ski-in/ski-out access, with chairlifts visible from your unit. The condo features a queen-sized Murphy bed, built-in bunk beds, full bathroom, living room equipped with a gas fireplace, and a compact kitchen. Additionally, you can easily walk to nearby restaurants and shops. The property is also situated on the shuttle route for added accessibility.

Guest favourite
An open living area showcases a comfortable seating arrangement with gray sofas, complemented by a light coffee table. A dining table with wooden chairs is positioned near the well-equipped kitchen, featuring wooden cabinetry and modern appliances. Windows allow natural light to brighten the space.
Apartment in Carrabassett Valley
4.86 out of 5 average rating, 29 reviews

*New Listing* Sugarloaf Ski In/Out Condo

Snowbrook Village Condo with 2 bedrooms, 2 bathrooms and 1 sofa bed. Can host 5-7 people. Perfect place to spend time outside during the day and relax by the fireplace in the evening. Kitchen is well outfitted so you need only bring your food and outdoor gear. Just a few steps away from the Snubber chairlift with pool and hot tubs available in the Village. Outside locker for your ski/golf equipment. Golf course, mountain bike trails, hiking and more nearby. Air conditioned in the summer.

Superhost
A bright open living space is furnished with a plush Queen bed adorned with a red throw blanket. A cozy armchair and spacious sectional sofa complement the area. Natural light filters through two windows, and a doorway leads to a full bath.
Loft in Palmyra
4.78 out of 5 average rating, 23 reviews

Golfer's Getaway - Luxury Studio Next to 1st Tee

A retreat in the middle of Fogg Brook Resort, it's the perfect spot for a buddies golf trip or a couple’s getaway. Steps from the 1st tee of our 18-hole course & driving range; next to Foggy’s Pub and a well-stocked pro shop, you’re in the heart of all the fun. In addition to honing your golf skills and enjoying delicious food & drink, access the other resort amenities including an in-ground swimming pool, walking trails, indoor / outdoor games, live music, and frequent special events.

Superhost
A cozy living area features a real wood fireplace with a brick surround and a television mounted above it. A plush red sofa with decorative pillows faces the fireplace, complemented by a coffee table designed for games. A door leads to a bedroom area in the background.
Condo in Carrabassett Valley
4.84 out of 5 average rating, 43 reviews

Sugarloaf w/ Pool, Hot Tub, Shuttle & Trail Access

A great two bedroom, two bathroom condo located on Sugarloaf Mountain directly on the Shuttle Route. Park your car when you arrive and leave it! Walk to the lift across the parking lot or grab the shuttle right outside your door to get to the main lodge, restaurants, bars, groceries, Sugarloaf Outdoor Center, and the list goes on! Apres ski at any number of the hot spots then head for the heated indoor pool house for a swim. Mountain Bike trails network right outside your door!

Top Guest favourite
A warm bedroom is presented with a spacious log bed, dressed in plaid bedding. Soft lighting from two bedside lamps creates a cozy atmosphere, while a window offers a view of the surrounding wooded area. A decorative 'SKI' sign adds a playful touch.
Townhouse in Carrabassett Valley
4.9 out of 5 average rating, 51 reviews

Sugarloaf Mt: on the mountain, pool, hot tub

Note: the sauna and hot tubs are NOT available in the summer and fall. On a dead-end street abutting Brackett Brook in Snowbrook Village, it is quiet and secluded. We are right next to the cross-country skiing, walking/hiking, mountain biking and snowshoeing trails. Walk approximately 700’ (2-3 minutes) to the Snubber ski lift or take the free shuttle that stops at the corner of the road and our parking lot every 20-30 minutes, depending on time of day.

Superhost
A spacious balcony is highlighted by two blue chairs facing a panoramic view of the surrounding landscape. Vibrant autumn foliage is visible in the distance, set against a cloudy sky. The wooden deck features weathered boards and offers a peaceful outdoor space.
Condo in Jackman
4.8 out of 5 average rating, 5 reviews

Grab Your Snow Boots | Escape to Jackman

Need a break from the daily grind? This lodge room in Jackman, Maine, offers a quiet, comfortable stay. Surrounded by snowy or autumn forests, it’s a great spot to slow down and enjoy the season. Local Adventures Nearby Jackman is a hub for outdoor activities Snowmobile rentals Guided hunting tours for bear, deer, moose & upland birds Great for trail exploring, wildlife, and winter sports Ideal for unplugging and reconnecting with nature

Guest favourite
Chalet in Carrabassett Valley
4.99 out of 5 average rating, 67 reviews

Cozy Chalet, 10-Min Drive to Sugarloaf, Sleeps 9

Entire chalet to yourself! 10 Min. drive or shuttle bus to Sugarloaf! Guests will have a great time staying at this cozy home located in a fun and quiet neighborhood right off Route 27. Great for all four seasons! Fish, hunt, hike, golf, and bike while its warm and ski, snowmobile, or cross country ski while the snow flies! A quick walk to a playground, pool, tennis & basketball courts, and the Carrabassett River.

Guest favourite
A single-story home is set against a backdrop of tall trees, featuring a front porch with white railings. The well-maintained lawn is complemented by a curved garden bed with mulch and shrubs, creating a welcoming exterior.
Home in Skowhegan
4.93 out of 5 average rating, 15 reviews

Home away from home

Skowhegan, Maine is centrally located to everything. It offers both a vibrant and unique downtown with close proximity to outdoor recreational areas. The Kennebec River runs through Skowhegan’s charming downtown area, and the town is easy to navigate. Pedestrian friendly sidewalks, downtown green spaces, and beautiful facades are worth the trip. Skowhegan has something for everyone.

Popular amenities for Somerset County rentals with a pool