Vacation rentals in Milton

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Top-rated vacation rentals in Milton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Tiny home in Wentworth
4.99 out of 5 average rating, 200 reviews

Tiny Riverfront A-Frame w/ Mountain Views, Hot Tub

Welcome to 'The Alexander' @ Casa de Moraga! This tiny A-frame is nestled on the bank of Baker River w/ breathtaking views of the river & White Mountains. Full kitchen, bathroom w/ shower & living/dining area. Wake up in the loft bedroom & see the mountains & river from bed. Read on the couch & enjoy the gel fuel fireplace, take a swim or fish in the river - relax in your private hot tub on the deck overlooking the river! 10 min to Tenney MTN. 35 min to Ice Castles, Franconia, Loon & Waterville!

Guest favorite
A weathered sign reading 'Rose Cottage' hangs from a tree, with vibrant autumn leaves surrounding the area. A quiet road is visible in the background, framed by trees, creating a serene and inviting atmosphere.
Guest suite in Lebanon
4.97 out of 5 average rating, 208 reviews

Rustic Rose Cottage of Historic West Lebanon

Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford
4.91 out of 5 average rating, 584 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Top guest favorite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton
4.99 out of 5 average rating, 166 reviews

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

Top guest favorite
The living area features a blend of comfortable seating, including a dark brown recliner and a soft sofa. A wooden coffee table is centrally placed, adorned with decorative items. Natural light illuminates the space, complemented by neutral walls and subtle décor.
Home in Lebanon
4.95 out of 5 average rating, 323 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Guest favorite
The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.
Home in Naples
4.98 out of 5 average rating, 178 reviews

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Top guest favorite
A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.
Cottage in Middleton
4.97 out of 5 average rating, 169 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Top guest favorite
A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.
Guesthouse in Hiram
5 out of 5 average rating, 131 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Top guest favorite
A vibrant sunset unfolds across the horizon, showcasing a gradient of orange, pink, and purple hues against a backdrop of silhouette trees and distant hills. Snow covers much of the ground, reflecting the colors of the sky.
Home in Wakefield
4.96 out of 5 average rating, 112 reviews

Cozy Lakes Region Escape. Fire Pit. Patio

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

Top guest favorite
A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.
Cottage in Middleton
4.96 out of 5 average rating, 225 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Top guest favorite
Home in Acton
4.95 out of 5 average rating, 369 reviews

The LOTUS welcomes you, stay a while

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna, heated seasonal outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding and a single fold out foam mattress on the 1st floor, that was just finished as another relax area, with 70" TV, record player, hammock & hanging chair.

Top guest favorite
A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.
Home in South Berwick
5 out of 5 average rating, 130 reviews

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Popular amenities for Milton vacation rentals

When is the best time to visit Milton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$47,488 GYDG$52,300 GYDG$51,045 GYDG$50,208 GYDG$52,927 GYDG$54,183 GYDG$65,688 GYDG$67,780 GYDG$54,601 GYDG$53,973 GYDG$50,417 GYDG$57,530 GYD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Milton?

    Four-legged friends are welcome in Milton. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Milton?

    Yes! Work meets play with ease at over 30 vacation rentals in Milton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Milton vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Milton, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly house rentals in Milton?

    Milton has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Milton?

    Experience the best of Milton with our cabin rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Milton have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Milton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Milton have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Milton. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Milton?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Milton

  • Total vacation rentals

    Explore 70 vacation rentals in Milton

  • Nightly prices starting at

    Milton vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Milton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Lake access, Gym, and BBQ grill across Milton rentals

  • 4.9 Average rating

    Milton stays are highly rated by guests—averaging 4.9 out of 5!

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