Raymond vacation rentals

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Top-rated vacation rentals in Raymond

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Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 165 reviews

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Mar 22 – 29

G$32,119 GYD per night

Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

Jul 15 – 22

G$25,305 GYD per night

Guest favorite

Loft in Bridgton

4.95 out of 5 average rating, 551 reviews

Tap House Loft~Sunny & Spacious, Private Hot Tub

Conveniently located in the heart of Downtown Bridgton, the Tap House Loft is ready for you, your friends and your family to enjoy! Walk to vibrant Main Street, Pondicherry Park, the Magic Lantern Theater, Highland Lake and all the downtown shops, gallerias and restaurants...or simply relax in the peace and quiet of our newly restored, historic warehouse. Located above the Sundown Lounge, this 900 sq ft space offers a large Master Suite with French Doors leading to a deck and hot tub.

Jan 13 – 20

G$35,898 GYD per night

Guest favorite

Cabin in Raymond

4.93 out of 5 average rating, 144 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Oct 2 – 9

G$38,277 GYD per night

Superhost

Farm stay in Gray

4.88 out of 5 average rating, 241 reviews

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Jun 16 – 21

G$42,843 GYD per night

Guest favorite

Home in Lewiston

4.99 out of 5 average rating, 138 reviews

Clean and comfortable home

First floor of newly renovated, well-stocked, single-family home in quiet, safe neighborhood. Full kitchen, 2 bedrooms each with comfortable queen-sized bed, full bathroom, on-site laundry. Shoppable art on-site :) Located less than 1 mi from Bates College and St. Mary’s Hospital. Less than 2 mi from Central Maine Medical Center. Proof of Covid-19 vaccination may be requested for all eligible to receive vaccine (including children).

May 2 – 9

G$23,516 GYD per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 218 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

May 29 – Jun 5

G$26,381 GYD per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Nov 2 – 9

G$24,002 GYD per night

Guest favorite

Cabin in Raymond

4.96 out of 5 average rating, 164 reviews

Idyllic Lakeside Cabin

Situated on a beautiful lake with 350 feet of private shoreline the cabin is ideal for family gatherings or a small group of friends, it is not available for parties and events. A seven day minimum stay is required for summer months. Cozy up with board games, a book and enjoy the tranquility. We have firewood on the property for you to use. The docks are not in the water from October to April.

Oct 4 – 11

G$117,483 GYD per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 197 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

G$14,519 GYD per night

Guest favorite

Guest suite in Lewiston

4.97 out of 5 average rating, 191 reviews

Sanctuary in the City

Welcome to our sanctuary in the city. Conveniently located just off the I-95, our spacious one-bedroom suite offers a queen bed, bath with cedar sauna, kitchenette, private yard with pergola, and laundry. Enjoy quick access to a range of local shops & restaurants, endless outdoor activities, and convenient access to Portland and Southern Maine’s coastal region.

Mar 20 – 27

G$28,448 GYD per night

Guest favorite

Farm stay in Gray

4.94 out of 5 average rating, 247 reviews

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

Mar 2 – 9

G$29,888 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Raymond vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Raymond's top sights

Seacoast Adventure59 locals recommend

Point Sebago6 locals recommend

Walmart Supercenter14 locals recommend

Bob's Seafood43 locals recommend

Pat's Pizza23 locals recommend

Applebee's Grill + Bar4 locals recommend

Other great vacation rentals in Raymond

Guest favorite

Cabin in Lovell

4.97 out of 5 average rating, 254 reviews

Secluded, cozy cabin nestled in the Maine woods

Nov 22 – 29

G$23,701 GYD per night

Guest favorite

Cottage in Bridgton

4.89 out of 5 average rating, 188 reviews

Rustic Pebble Cottage in beautiful Bridgton, Maine

Nov 20 – 27

G$21,410 GYD per night

Guest favorite

Guest suite in Raymond, Maine

4.91 out of 5 average rating, 122 reviews

Rustic knotty pine getaway

Aug 19 – 26

G$49,459 GYD per night

Guest favorite

Apartment in Casco

4.9 out of 5 average rating, 30 reviews

Country Village Getaway

Dec 12 – 19

G$23,792 GYD per night

Guest favorite

Cottage in Raymond

4.95 out of 5 average rating, 22 reviews

Relaxing New England Lakeside Getaway

Oct 11 – 18

G$50,885 GYD per night

Guest favorite

Home in Windham

4.95 out of 5 average rating, 65 reviews

Waterfront Gem walkable to Restaurants!

Mar 16 – 23

G$34,558 GYD per night

Guest favorite

Cottage in Raymond

4.9 out of 5 average rating, 90 reviews

Relax by a Quiet Lake

May 13 – 20

G$32,107 GYD per night

Guest favorite

Home in Raymond

5.0 out of 5 average rating, 29 reviews

Cheerful 3 Bedroom Home for your Maine Getaway

May 29 – Jun 5

G$47,108 GYD per night

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Other great vacation rentals in Raymond

Guest favorite

Vacation home in Raymond

5.0 out of 5 average rating, 17 reviews

Cedar Lane Lodge - Luxury Lake House

Dec 11 – 18

G$207,443 GYD per night

Guest favorite

Guest suite in Pownal

4.97 out of 5 average rating, 73 reviews

Maine Mystic Gardens, Family Friendly Suite

May 17 – 24

G$21,497 GYD per night

Guest favorite

Home in Gray

5.0 out of 5 average rating, 18 reviews

Little Sebago Lakefront Getaway

Nov 3 – 10

G$43,666 GYD per night

Guest favorite

Cottage in Raymond

4.89 out of 5 average rating, 19 reviews

Hawthorne Cottages Lakeside

Jun 10 – 17

G$40,183 GYD per night

Guest favorite

Cabin in Naples

4.89 out of 5 average rating, 84 reviews

Songo Lock Cabins #2

Nov 25 – Dec 2

G$28,609 GYD per night

Guest favorite

Cabin in Bridgton

4.9 out of 5 average rating, 39 reviews

Rustic Elegance: a glamping getaway

Oct 21 – 28

G$24,404 GYD per night

Guest favorite

Apartment in Gray

4.94 out of 5 average rating, 82 reviews

Two bedroom duplex across st from crystal lake

Nov 6 – 13

G$28,733 GYD per night

Guest favorite

Vacation home in Raymond

5.0 out of 5 average rating, 13 reviews

Paradise Point on Panther Pond

Nov 23 – 30

G$158,952 GYD per night

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Quick stats about vacation rentals in Raymond

Total rentals
290 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
5.9K reviews
Nightly prices starting at
G$10,424 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Raymond?
Yes! Work meets play with ease at over 130 vacation rentals in Raymond featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Raymond?
Four-legged friends are welcome in Raymond. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Raymond?
Raymond has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Raymond have a bbq area?
Absolutely! We offer over 50 cottage rentals with a bbq area in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Raymond have wifi?
Absolutely! We offer over 70 cottage rentals with wifi in Raymond. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cabin rentals in Raymond?
Experience the best of Raymond with our cabin rentals, starting at about $90 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 Raymond have a gym?
Absolutely! We offer over 10 house rentals with a gym in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Raymond have air conditioning?
Absolutely! We offer over 90 house rentals with air conditioning in Raymond. Enjoy a tailored experience with all the comforts you desire.

Raymond vacation rentals

Top-rated vacation rentals in Raymond

Vacation rentals for every style

Cottages

Cabins

Houses

Popular amenities for Raymond vacation rentals

Stay near Raymond's top sights

Other great vacation rentals in Raymond

Cabin in Lovell

Cottage in Bridgton

Guest suite in Raymond, Maine

Apartment in Casco

Cottage in Raymond

Home in Windham

Cottage in Raymond

Home in Raymond

Other great vacation rentals in Raymond

Vacation home in Raymond

Guest suite in Pownal

Home in Gray

Cottage in Raymond

Cabin in Naples

Cabin in Bridgton

Apartment in Gray

Vacation home in Raymond

Quick stats about vacation rentals in Raymond

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Raymond?

Are there pet-friendly vacation rentals in Raymond?

Are there family-friendly house rentals in Raymond?

Do cottage rentals in Raymond have a bbq area?

Do cottage rentals in Raymond have wifi?

How much does it cost to stay in cabin rentals in Raymond?

Do house rentals in Raymond have a gym?

Do house rentals in Raymond have air conditioning?

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